TWI547724B - Color filter, liquid crystal display device, and method for fabricating color filter - Google Patents
Color filter, liquid crystal display device, and method for fabricating color filter Download PDFInfo
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- TWI547724B TWI547724B TW101125215A TW101125215A TWI547724B TW I547724 B TWI547724 B TW I547724B TW 101125215 A TW101125215 A TW 101125215A TW 101125215 A TW101125215 A TW 101125215A TW I547724 B TWI547724 B TW I547724B
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- compound
- color filter
- acid
- film
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 140
- 238000000034 method Methods 0.000 title claims description 107
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- 238000004040 coloring Methods 0.000 claims description 148
- 239000000203 mixture Substances 0.000 claims description 144
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- 239000000049 pigment Substances 0.000 claims description 133
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- 239000000758 substrate Substances 0.000 claims description 91
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- 239000011347 resin Substances 0.000 claims description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 64
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- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 238000011907 photodimerization Methods 0.000 description 1
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- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
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- 150000003077 polyols Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
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- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
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- ZSLKNYNUPNHOLY-UHFFFAOYSA-N purine-2,7-diamine Chemical compound NC1=NC=C2N(C=NC2=N1)N ZSLKNYNUPNHOLY-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- GZTPJDLYPMPRDF-UHFFFAOYSA-N pyrrolo[3,2-c]pyrazole Chemical compound N1=NC2=CC=NC2=C1 GZTPJDLYPMPRDF-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
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- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
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- LJZVDOUZSMHXJH-UHFFFAOYSA-K ruthenium(3+);triiodide Chemical compound [Ru+3].[I-].[I-].[I-] LJZVDOUZSMHXJH-UHFFFAOYSA-K 0.000 description 1
- LFRAUWYBZMOKBC-UHFFFAOYSA-N samarium tungsten Chemical compound [Sm][W] LFRAUWYBZMOKBC-UHFFFAOYSA-N 0.000 description 1
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- 125000005920 sec-butoxy group Chemical group 0.000 description 1
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- 239000005361 soda-lime glass Substances 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- NETSNTQRMHVIEK-UHFFFAOYSA-M sodium;2-[n-butyl-4-[[4-[butyl(2-sulfonatoethyl)azaniumylidene]cyclohexa-2,5-dien-1-ylidene]-[4-(4-ethoxyanilino)phenyl]methyl]anilino]ethanesulfonate Chemical compound [Na+].C1=CC(N(CCS([O-])(=O)=O)CCCC)=CC=C1C(C=1C=CC(NC=2C=CC(OCC)=CC=2)=CC=1)=C1C=CC(=[N+](CCCC)CCS([O-])(=O)=O)C=C1 NETSNTQRMHVIEK-UHFFFAOYSA-M 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-N sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-N 0.000 description 1
- RWVGQQGBQSJDQV-UHFFFAOYSA-M sodium;3-[[4-[(e)-[4-(4-ethoxyanilino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]-2-methylcyclohexa-2,5-dien-1-ylidene]methyl]-n-ethyl-3-methylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C(=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=2C(=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=C1 RWVGQQGBQSJDQV-UHFFFAOYSA-M 0.000 description 1
- KQRZWHVIXVADGL-UHFFFAOYSA-M sodium;4-[[4-(dibenzylamino)phenyl]-(4-dibenzylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]benzene-1,3-disulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(S(=O)(=O)[O-])=CC=C1C(C=1C=CC(=CC=1)N(CC=1C=CC=CC=1)CC=1C=CC=CC=1)=C(C=C1)C=CC1=[N+](CC=1C=CC=CC=1)CC1=CC=CC=C1 KQRZWHVIXVADGL-UHFFFAOYSA-M 0.000 description 1
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- WNQPPENQFWLADQ-UHFFFAOYSA-J tetrasodium;4-hydroxy-5-[[4-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]carbamoylamino]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(O)=C2C(N=NC3=C(C)C=C(C(=C3)OC)NC(=O)NC3=CC(C)=C(N=NC=4C5=C(O)C=C(C=C5C=C(C=4)S([O-])(=O)=O)S([O-])(=O)=O)C=C3OC)=CC(S([O-])(=O)=O)=CC2=C1 WNQPPENQFWLADQ-UHFFFAOYSA-J 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
- VRVDFJOCCWSFLI-UHFFFAOYSA-K trisodium 3-[[4-[(6-anilino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].COc1cc(N=Nc2cc(c3cccc(c3c2)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O VRVDFJOCCWSFLI-UHFFFAOYSA-K 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
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- 239000010937 tungsten Substances 0.000 description 1
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- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
- XOSXWYQMOYSSKB-UHFFFAOYSA-L water blue Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=C(N)C(C)=CC(C(=C2C=CC(C=C2)=NC=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S(O)(=O)=O)=CC=2)=C1 XOSXWYQMOYSSKB-UHFFFAOYSA-L 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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- 125000005023 xylyl group Chemical group 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/1025—Preparatory processes from tetracarboxylic acids or derivatives and diamines polymerised by radiations
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Description
本發明涉及一種彩色濾光片、液晶顯示元件及彩色濾光片的製造方法。 The present invention relates to a color filter, a liquid crystal display element, and a method of manufacturing a color filter.
液晶顯示元件包含在玻璃基板等一對基板中夾持有液晶而構成的液晶面板。在夾持液晶的基板的表面可設置配向膜。自先前起通過如下方式而賦予配向膜液晶配向控制能力:使用聚醯亞胺等化學性穩定且具有高的耐熱性的有機膜,實施用尼龍或聚酯等布而於一個方向上進行摩擦的摩擦處理。 The liquid crystal display element includes a liquid crystal panel in which liquid crystal is sandwiched between a pair of substrates such as a glass substrate. An alignment film may be provided on the surface of the substrate sandwiching the liquid crystal. The aligning film liquid crystal alignment control ability is imparted from the prior art by using an organic film which is chemically stable and has high heat resistance such as polyimide, and is rubbed in one direction by a cloth such as nylon or polyester. Friction treatment.
於液晶顯示元件的一對基板間,通過散佈等而配置包含玻璃、氧化鋁或樹脂的球狀或棒狀的間隔件,將液晶的厚度保持為1 μm~20 μm左右的規定值。於液晶顯示元件中,產生液晶的配向變化,對自背光源或外光等光源所放射的光發揮作為微細的光閘(shutter)的功能。而且,使光部分性透過或遮光而進行顯示。液晶顯示元件具有薄型、輕量等優異的特徵。 A spherical or rod-shaped spacer including glass, alumina, or resin is disposed between a pair of substrates of the liquid crystal display device by dispersion or the like, and the thickness of the liquid crystal is maintained at a predetermined value of about 1 μm to 20 μm. In the liquid crystal display device, the alignment change of the liquid crystal occurs, and the light emitted from the light source such as the backlight or the external light functions as a fine shutter. Further, the light is partially transmitted or blocked to display. The liquid crystal display element is characterized by being thin, lightweight, and the like.
液晶顯示元件在開發的當初是用作以字符顯示等為中心的計算器或時鐘的顯示元件。其後,由於變得可進行大畫面中的點陣顯示,因此將用途擴大至筆記本電腦的顯示元件等中。 The liquid crystal display element was originally developed as a display element of a calculator or a clock centered on a character display or the like. Thereafter, since dot matrix display in a large screen can be performed, the use is expanded to a display element of a notebook computer or the like.
另外,液晶顯示元件克服了高精細化、彩色化及視角擴大等課題,將用途進一步擴大到PC(個人電腦)的顯示 器用途中。於最近,實現了更廣的視角或液晶的高速響應化或顯示品質的提高等,從而用作大型的薄型電視用顯示元件。 In addition, the liquid crystal display device overcomes the problems of high definition, colorization, and viewing angle expansion, and further expands its use to display of PCs (personal computers). In use. Recently, a wider viewing angle, a high-speed response of a liquid crystal, an improvement in display quality, and the like have been realized, and it has been used as a display element for a large-sized thin television.
可實現此種液晶顯示元件的發展的技術之一是如上所述的可實現彩色顯示的彩色化技術。 One of the techniques for realizing the development of such a liquid crystal display element is the colorization technique which realizes color display as described above.
液晶顯示元件通常不能以其自身顯色,從而難以進行彩色顯示。因此,開發了利用彩色濾光片的技術,液晶顯示元件變得可實現彩色顯示。 Liquid crystal display elements generally cannot develop color by themselves, making it difficult to perform color display. Therefore, technology using color filters has been developed, and liquid crystal display elements have become color-displayable.
另外,使用彩色濾光片的彩色化技術亦可用於使用白色發光層的有機電致發光(Electroluminescence,EL)元件或電子紙等的彩色顯示中。另外,若利用彩色濾光片,則變得可進行電荷耦合元件(Charge Coupled Device,CCD)圖像感測器、互補型金屬氧化物半導體(Complementary Metal Oxide Semiconductor,CMOS)圖像感測器等固體攝像元件的彩色攝影。 Further, the coloring technique using a color filter can also be used for color display of an organic electroluminescence (EL) element or an electronic paper using a white light-emitting layer. Further, when a color filter is used, a charge coupled device (CCD) image sensor, a complementary metal oxide semiconductor (CMOS) image sensor, or the like can be used. Color photography of solid-state imaging elements.
彩色濾光片包含玻璃等透明基板與紅、綠及藍等的微小著色圖案。著色圖案採用格子狀等規則形狀而排列於透明基板上。 The color filter includes a transparent substrate such as glass and a minute colored pattern of red, green, and blue. The coloring patterns are arranged on a transparent substrate in a regular shape such as a lattice shape.
彩色濾光片的製造方法例如已知有如下所述的方法。於透明基板上或者形成有所期望的圖案的遮光層的透明基板上,塗布適當的可感應照射線的著色組成物。著色組成物可使用在著色劑中包含紅、綠、藍等的顏料的顏料分散型著色感放射線性組成物。其次,使塗膜乾燥後,介隔掩模而對乾燥塗膜照射放射線(以下稱為“曝光”),實 施顯影處理。然後,進行例如230℃等超過200℃的高溫下的硬化,通過該些操作而獲得定影的著色圖案(例如參照專利文獻1或專利文獻2)。於著色圖案上形成例如透明的電極,於其上形成上述的配向膜。 As a method of manufacturing a color filter, for example, the method described below is known. A colored composition of an appropriate inductive illumination line is applied to a transparent substrate or a transparent substrate on which a light-shielding layer having a desired pattern is formed. As the coloring composition, a pigment dispersion type coloring radiation-sensitive linear composition containing a pigment such as red, green, or blue in the coloring agent can be used. Next, after drying the coating film, the dried coating film is irradiated with radiation (hereinafter referred to as "exposure") through a mask. Development treatment. Then, the curing at a high temperature of, for example, 230 ° C or higher is performed at a high temperature, and a fixed color pattern is obtained by these operations (for example, refer to Patent Document 1 or Patent Document 2). For example, a transparent electrode is formed on the colored pattern, and the above alignment film is formed thereon.
近年來,對於顯示元件的高畫質化及高亮度化的要求日益變高,對於彩色濾光片也強烈要求能夠有助於此種性能提高。為了實現顯示元件的高對比度化或固體攝像元件的高精細化,有效的是使用染料作為著色劑(例如參照專利文獻3~專利文獻5)。於彩色濾光片中,使用染料作為著色劑的技術也受到關注。在包含染料的先前的著色組成物中,主要採用將多官能丙烯酸酯、烷氧基甲基三聚氰胺樹脂等與聚合起始劑加以組合的硬化方法。 In recent years, there has been an increasing demand for high image quality and high luminance of display elements, and there is a strong demand for color filters to contribute to such performance improvement. In order to achieve high contrast of the display element or high definition of the solid-state imaging element, it is effective to use a dye as a coloring agent (for example, refer to Patent Document 3 to Patent Document 5). Among color filters, a technique using a dye as a colorant has also been attracting attention. In the prior coloring composition containing a dye, a hardening method in which a polyfunctional acrylate, an alkoxymethyl melamine resin, or the like is combined with a polymerization initiator is mainly used.
然而,在使用包含染料的先前的著色組成物而形成的著色圖案中存在如下的問題:與使用包含顏料的著色組成物的著色圖案相比而言,可靠性差。此種問題是由於如下原因而造成的:著色劑中所使用的染料的耐熱性或耐光性差,容易受到加熱或紫外線照射而劣化。因此,於必需高溫下的硬化步驟的彩色濾光片的著色圖案的形成步驟中,染料及使用其的著色圖案的耐熱性亦成為問題。 However, there is a problem in the coloring pattern formed using the previous coloring composition containing the dye that the reliability is poor as compared with the coloring pattern using the coloring composition containing the pigment. Such a problem is caused by the fact that the dye used in the colorant is inferior in heat resistance and light resistance, and is easily deteriorated by heating or ultraviolet irradiation. Therefore, in the step of forming the colored pattern of the color filter in the hardening step at a high temperature, the heat resistance of the dye and the colored pattern using the same also becomes a problem.
而且,於彩色濾光片中,關於著色圖案上所設的配向膜,亦進行了改善,於近年來開始關注光配向技術。如上所述,先前的液晶顯示元件的配向膜使用聚醯亞胺等化學性穩定且具有高的耐熱性的有機膜,通過用布擦其表面的摩擦而進行配向處理。然而,自開發當初起,除了隨著摩 擦處理而產生塵埃或異物以外,亦指出了產生使液晶顯示元件的顯示品質降低的配向膜上的傷痕的問題。另外,隨著最近的液晶顯示元件的高精細化,基板上的開關主動元件或電極等構成元件也微細化,由於該些而引起基板上的凹凸也變得微細,於基板的整個面進行配向膜的均一的摩擦處理的操作變困難。因此,變得強烈要求無摩擦的配向處理技術。 Further, in the color filter, the alignment film provided on the coloring pattern has also been improved, and in recent years, attention has been paid to the optical alignment technique. As described above, the alignment film of the conventional liquid crystal display element uses an organic film which is chemically stable such as polyimide and has high heat resistance, and is subjected to alignment treatment by rubbing the surface with rubbing. However, since the beginning of the development, in addition to In addition to dust or foreign matter generated by the rubbing treatment, there is also a problem that a flaw on the alignment film which lowers the display quality of the liquid crystal display element is caused. In addition, with the recent refinement of the liquid crystal display device, the components such as the switching active device or the electrode on the substrate are also miniaturized, and the unevenness on the substrate is also fined, and the alignment is performed on the entire surface of the substrate. The uniform rubbing treatment of the film becomes difficult. Therefore, there has been a strong demand for a frictionless alignment treatment technique.
光配向技術是使用光的無摩擦的配向處理技術,例如自規定方向對配向膜照射紫外區域的偏光的光。而且,是在配向膜中產生光反應,於該配向膜表面導入各向異性而賦予液晶配向控制能力的技術。另外,有時將利用光配向技術所得的配向膜特別稱為光配向膜。 The photoalignment technique is a frictionless alignment treatment technique using light, such as polarized light that illuminates the alignment film from the ultraviolet region from a prescribed direction. Further, it is a technique in which a photoreaction is generated in the alignment film, and anisotropy is introduced to the surface of the alignment film to impart alignment control ability to the liquid crystal. Further, an alignment film obtained by a photo-alignment technique is sometimes referred to as a photo-alignment film.
光配向處理的方法已知有光交聯型或光分解型的光配向技術(例如參照非專利文獻1)。光交聯型例如是對包含聚乙烯醇肉桂酸酯衍生物的配向膜照射偏光紫外線,利用光二聚化(photodimerization)而產生交聯反應,從而於配向膜中導入各向異性。 A photo-alignment type or a photo-decomposition type photo-alignment technique is known as a method of photo-alignment processing (see, for example, Non-Patent Document 1). The photocrosslinking type is, for example, a polarizing ultraviolet ray is applied to an alignment film containing a polyvinyl cinnamate derivative, and a cross-linking reaction is generated by photodimerization to introduce anisotropy into the alignment film.
而且,光分解型例如是對包含聚醯亞胺的配向膜照射偏光紫外線,於配向膜中各向異性地產生光分解反應,從而於配向膜中導入各向異性。該光分解型光配向技術可使用化學性穩定且具有高的耐熱性而自先前起便使用的聚醯亞胺配向膜,因此是更優選的光配向技術。 Further, the photodecomposition type is, for example, by irradiating a polarizing ultraviolet ray to an alignment film containing polyimine, and anisotropically generating a photodecomposition reaction in the alignment film to introduce anisotropy into the alignment film. This photo-decomposable photo-alignment technique is a more preferable photo-alignment technique because it can use a polyimide-alignment film which is chemically stable and has high heat resistance and has been used since the prior art.
[專利文獻1]日本專利特開平2-144502號公報 [Patent Document 1] Japanese Patent Laid-Open No. Hei 2-144502
[專利文獻2]日本專利特開平3-53201號公報 [Patent Document 2] Japanese Patent Laid-Open No. 3-53201
[專利文獻3]日本專利特開2005-99584號公報 [Patent Document 3] Japanese Patent Laid-Open Publication No. 2005-99584
[專利文獻4]日本專利特開2007-219466號公報 [Patent Document 4] Japanese Patent Laid-Open Publication No. 2007-219466
[專利文獻5]日本專利特開2007-316179號公報 [Patent Document 5] Japanese Patent Laid-Open Publication No. 2007-316179
[非專利文獻1]M.Shadt等人,日本應用物理雜誌(Jpn.J.Appl.Phys.)31,2155(1992) [Non-Patent Document 1] M. Shadt et al., Jpn. J. Appl. Phys. 31, 2155 (1992)
如上所述,雖然是推進技術開發的液晶顯示元件,但要求更進一步的高畫質化及顯示品質的提高。因此,液晶顯示元件變得必須確實地採用所開發的新技術。特別是關於作為重要的構成元件的彩色濾光片,要求應用新穎的高畫質化技術或顯示品質的提高技術,例如於著色劑中使用上述染料的著色圖案的形成技術或配向膜的光配向技術等。 As described above, although it is a liquid crystal display element developed by the advancement technology, further improvement in image quality and display quality is required. Therefore, the liquid crystal display element has become necessary to surely adopt the new technology developed. In particular, as a color filter which is an important constituent element, it is required to apply a novel high image quality technique or a technique for improving display quality, for example, a coloring pattern forming technique using the above dye in a colorant or a light alignment of an alignment film. Technology, etc.
現狀是上述技術具有各自的課題,無法直接採用各技術或者將該些技術僅僅加以組合而採用。 The current situation is that the above technologies have their own problems, and it is not possible to directly adopt each technology or to combine these technologies only.
例如,如上所述那樣,染料的耐熱性差,容易由於加熱而產生分解等劣化。因此,於由包含染料的先前的著色組成物而形成的著色圖案的彩色濾光片中,存在耐熱性差的問題,無法直接應用於先前的液晶顯示元件中。 For example, as described above, the heat resistance of the dye is poor, and deterioration due to decomposition or the like is likely to occur due to heating. Therefore, in the color filter of the colored pattern formed by the previous coloring composition containing the dye, there is a problem that heat resistance is poor, and it cannot be directly applied to the prior liquid crystal display element.
而且,於著色劑中使用染料的彩色濾光片中,對著色圖案上所形成的配向膜進行使用光配向技術的配向處理時,染料的耐光性差,存在如下的可能:受到配向膜上所 照射的紫外線的照射而造成染料分解等劣化。特別是於上述的光分解型的光配向技術中,必需使構成配向膜的有機膜分解,因此使用紫外線作為照射光,對耐光性差的染料的影響變大。 Further, in the color filter using a dye in the colorant, when the alignment film formed on the colored pattern is subjected to an alignment treatment using a photo-alignment technique, the light resistance of the dye is poor, and there is a possibility that it is subjected to an alignment film. Irradiation of the irradiated ultraviolet rays causes deterioration of dye decomposition or the like. In particular, in the photo-dissociation type optical alignment technique described above, it is necessary to decompose the organic film constituting the alignment film. Therefore, the use of ultraviolet rays as the irradiation light increases the influence on the dye having poor light resistance.
於著色圖案中的染料進行分解等而造成劣化時,在使用該彩色濾光片的液晶顯示元件中,擔心產生如下的問題。 When the dye in the colored pattern is decomposed or the like to cause deterioration, the liquid crystal display element using the color filter is likely to cause the following problems.
第一,產生彩色濾光片的褪色,從而存在有損包含使用染料的著色圖案的彩色濾光片的特徵中的顏色特性的優性的現象。 First, fading of the color filter is caused, so that there is a phenomenon that the color characteristics of the color filter including the coloring pattern using the dye are excellent.
第二,於著色圖案中的染料中產生分解時,存在如下的現象:生成高極性的雜質,該雜質溶出至液晶面板內的液晶中而使液晶顯示元件的顯示品質降低。液晶顯示元件的液晶如上所述那樣由一對基板各自之上所設的配向膜而夾持,受到配向控制。配向膜例如包含高極性結構的聚醯亞胺等的有機膜。因此,若液晶中所溶出的高極性的雜質增加,則存在該些雜質的一部分吸附於配向膜表面的情況。此種於配向膜表面上的高極性雜質的吸附有時會引起顯示不良現象,例如使液晶顯示元件的顯示品質降低的所謂的殘像現象等。 Second, when decomposition occurs in the dye in the colored pattern, there is a phenomenon in which impurities of high polarity are generated, and the impurities are eluted into the liquid crystal in the liquid crystal panel to lower the display quality of the liquid crystal display element. The liquid crystal of the liquid crystal display element is sandwiched by the alignment film provided on each of the pair of substrates as described above, and is subjected to alignment control. The alignment film is, for example, an organic film containing a polyimide having a highly polar structure. Therefore, if the highly polar impurities eluted in the liquid crystal increase, a part of the impurities may be adsorbed on the surface of the alignment film. Such adsorption of highly polar impurities on the surface of the alignment film may cause display failure, for example, a so-called afterimage phenomenon in which the display quality of the liquid crystal display element is lowered.
對於以上的問題,要求對其進行改善的技術開發。例如,為了抑制將染料作為著色劑的著色圖案的熱劣化,改善褪色的課題,有效的是於著色圖案的硬化步驟中,實現更低溫的加熱。 For the above problems, technical development is required to improve them. For example, in order to suppress the thermal deterioration of the coloring pattern of the dye as a coloring agent and to improve the problem of fading, it is effective to achieve lower temperature heating in the curing step of the colored pattern.
在這種情況下,使用先前的著色組成物而由低溫的硬 化步驟所得的先前的著色圖案的彩色濾光片中,於耐顯影性、或於液晶顯示元件中應用時的電壓保持率等可靠性中無法實現充分的性能。可列舉其原因在於:先前的著色組成物的著色圖案的硬化反應性並不充分。 In this case, using the previous coloring composition and being hardened by low temperature In the color filter of the previous coloring pattern obtained by the chemical conversion step, sufficient performance cannot be achieved in reliability such as development resistance or voltage holding ratio when applied to a liquid crystal display element. The reason for this is that the curing reactivity of the coloring pattern of the previous coloring composition is not sufficient.
因此,要求使用可於低溫下硬化且可含有染料的著色組成物,實現可利用低溫的硬化步驟而製造的著色圖案。 Therefore, it is required to use a colored composition which can be cured at a low temperature and which can contain a dye, and realize a colored pattern which can be produced by a low-temperature hardening step.
而且,為了抑制以染料為著色劑的著色圖案的光劣化,改善褪色的課題,有效的是於彩色濾光片的著色圖案上設置保護著色圖案免受紫外線的層。 Further, in order to suppress the photodegradation of the colored pattern of the dye as a coloring agent and to improve the problem of fading, it is effective to provide a layer for protecting the colored pattern from ultraviolet rays on the colored pattern of the color filter.
在彩色濾光片的製造中,當形成著色圖案後,在成膜成為電極的ITO(Indium Tin Oxide:摻雜有錫的氧化銦)之前,可以在著色圖案上形成保護膜。以使基板的凹凸平坦化且實現優異特性的ITO電極的方式形成該保護膜。若亦可將該保護膜利用為用以保護著色圖案的層,則變得可保護著色圖案中所含的染料免受光配向處理時的紫外線。 In the production of the color filter, after the coloring pattern is formed, a protective film can be formed on the colored pattern before the formation of ITO (Indium Tin Oxide) which is an electrode. The protective film is formed in such a manner that the unevenness of the substrate is flattened and an ITO electrode having excellent characteristics is realized. If the protective film can also be used as a layer for protecting the colored pattern, it becomes possible to protect the dye contained in the colored pattern from ultraviolet rays at the time of photoalignment treatment.
另外,作為此種保護膜的配設,於著色圖案中的染料中產生分解,產生高極性的雜質的情況下,變得亦可實現抑制雜質溶出至液晶中的效果。 In addition, as the arrangement of such a protective film, decomposition of the dye in the colored pattern occurs, and when highly polar impurities are generated, the effect of suppressing elution of impurities into the liquid crystal can be achieved.
此處,為了形成保護膜,通常必需要硬化步驟。至於該硬化步驟中的加熱,在下層中存在使用包含染料的著色組成物而形成的著色圖案的情況時,存在引起著色圖案的劣化的擔憂。因此,理想的是保護膜是可於低溫的硬化步驟中形成的保護膜。 Here, in order to form a protective film, a hardening step is usually required. As for the heating in the hardening step, when there is a colored pattern formed by using the colored composition containing the dye in the lower layer, there is a fear that the colored pattern is deteriorated. Therefore, it is desirable that the protective film is a protective film which can be formed in a hardening step at a low temperature.
而且,為了抑制高極性的雜質吸附於配向膜表面上, 抑制使液晶顯示元件的顯示品質降低的顯示不良現象,變得必須使構成配向膜的有機膜的結構最佳化。亦即,有效的是一面維持配向膜的熱穩定性及化學穩定性等必要的特性,一面以抑制高極性雜質吸附於配向膜表面上的方式使結構最佳化。在這種情況下,如上所述地優選採用化學性穩定且耐熱性優異的聚醯亞胺膜作為配向膜,其中有效的是選擇使用低極性結構的聚醯亞胺的配向膜。而且,作為配向處理方法,有效的是選擇可應用於聚醯亞胺膜中的光分解型的光配向技術。 Moreover, in order to suppress adsorption of highly polar impurities on the surface of the alignment film, In order to suppress the display failure phenomenon which deteriorates the display quality of the liquid crystal display element, it is necessary to optimize the structure of the organic film constituting the alignment film. In other words, it is effective to optimize the structure while suppressing adsorption of highly polar impurities on the surface of the alignment film while maintaining necessary characteristics such as thermal stability and chemical stability of the alignment film. In this case, as described above, a polyimide film which is chemically stable and excellent in heat resistance is preferably used as the alignment film, and it is effective to select an alignment film of a polyimide having a low polarity structure. Further, as the alignment treatment method, it is effective to select a photo-dissociation type optical alignment technique which can be applied to a polyimide film.
根據以上而期望實現如下的彩色濾光片,所述彩色濾光片包含由可低溫硬化的著色組成物而形成的可含有染料的著色圖案、可應用光分解型等光配向處理技術的低極性結構配向膜。該彩色濾光片優選包含可通過低溫硬化而形成的保護膜。而且,強烈期望彩色濾光片的耐顯影性、耐熱性、耐溶劑性、電壓保持率等優異,使用該彩色濾光片的液晶顯示元件可實現高畫質化及高的顯示品質。 According to the above, it is desirable to realize a color filter including a dye-containing coloring pattern formed of a low-temperature-curable coloring composition, and a low polarity which can be applied to a photo-alignment processing technique such as a photodecomposition type. Structural alignment film. The color filter preferably contains a protective film which can be formed by low temperature hardening. Further, it is strongly desired that the color filter is excellent in development resistance, heat resistance, solvent resistance, voltage holding ratio, and the like, and the liquid crystal display element using the color filter can achieve high image quality and high display quality.
本發明是鑒於如上所述的問題而成的。亦即,本發明的目的在於提供一種彩色濾光片及該彩色濾光片的製造方法,所述彩色濾光片包含由可低溫硬化的著色組成物而形成的可於著色劑中包含染料的著色圖案、可進行光配向處理的低極性結構的配向膜。而且提供一種使用該彩色濾光片而構成的液晶顯示元件。 The present invention has been made in view of the above problems. That is, it is an object of the present invention to provide a color filter comprising a colorant-containing coloring composition and a dye-containing coloring agent, and a method of producing the color filter. A coloring pattern, an alignment film of a low polarity structure capable of photoalignment treatment. Further, a liquid crystal display element constructed using the color filter is provided.
而且,本發明的其他目的在於提供一種彩色濾光片及 該彩色濾光片的製造方法,所述彩色濾光片包含使用可低溫硬化的著色組成物而形成的可於著色劑中包含染料的著色圖案、通過低溫硬化而形成的保護膜、可進行光配向處理的低極性結構的配向膜。而且提供一種使用該彩色濾光片而構成的液晶顯示元件。 Moreover, another object of the present invention is to provide a color filter and In the method of producing a color filter, the color filter includes a colored pattern which can be formed by using a coloring composition which can be cured at a low temperature, a coloring pattern containing a dye in a coloring agent, a protective film formed by low-temperature curing, and light-receiving. An alignment film of a low polarity structure that is oriented to the treatment. Further, a liquid crystal display element constructed using the color filter is provided.
本發明的第1態樣涉及一種彩色濾光片,其特徵在於包含著色圖案與配向膜:所述著色圖案含有選自由二酮基吡咯並吡咯類顏料、鹵化鋅酞菁類顏料、三芳基甲烷類染料及偶氮類染料所構成的群組的至少1種著色劑;所述配向膜是對含有通式[a]所表示的結構單元的聚醯亞胺照射偏光的紫外線而形成的配向膜;
(通式[a]中,P1表示具有脂環族結構的4價有機基,P2表示2價有機基)。 (In the general formula [a], P 1 represents a tetravalent organic group having an alicyclic structure, and P 2 represents a divalent organic group).
在本發明的第1態樣中,優選表示聚醯亞胺所含有的結構單元的通式[a]的P1是選自由下述結構所構成的群組的至少1種結構;
(式中,P3、P4、P5及P6分別獨立地表示氫或碳數為1~4的有機基)。 (In the formula, P 3 , P 4 , P 5 and P 6 each independently represent hydrogen or an organic group having 1 to 4 carbon atoms).
在本發明的第1態樣中,著色圖案優選由含有如下化合物的著色組成物而形成:[I]鹼溶性樹脂、[II]具有乙烯性不飽和鍵的聚合性化合物、[III]感放射線性聚合起始劑、及[IV]所述著色劑。 In the first aspect of the invention, the colored pattern is preferably formed of a coloring composition containing a compound: [I] an alkali-soluble resin, [II] a polymerizable compound having an ethylenically unsaturated bond, and [III] radiation-sensitive. a polymerization initiator, and the colorant described in [IV].
在本發明的第1態樣中,優選著色組成物進一步含有[V]選自由下述式(1)所表示的化合物、下述式(2)所表示的化合物、三級胺化合物、胺鹽、鏻鹽、脒鹽、醯胺化合物、硫醇化合物、嵌段異氰酸酯化合物及含有咪唑環的化合物所構成的群組的至少1種化合物;[化3]
(式(1)中,R1~R6分別獨立為氫原子、吸電子基或胺基;其中,R1~R6中的至少1個是吸電子基,且R1~R6中的至少1個是胺基;而且,上述胺基的氫原子的全部或一部分也可以被碳數為1~6的烷基取代;式(2)中,R7~R16分別獨立為氫原子、吸電子基或胺基;其中,R7~R16中的至少1個是胺基;而且,上述胺基的氫原子的全部或一部分也可以被碳數為1~6的烴基取代;A為單鍵、羰基、羰氧基、羰基亞甲基、亞磺醯基、磺醯基、亞甲基或碳數為2~6的伸烷基;其中,上述亞甲基及伸烷基的氫原子的全部或一部分也可以被氰基、鹵素原子或氟烷基取代)。 (In the formula (1), R 1 to R 6 are each independently a hydrogen atom, an electron withdrawing group or an amine group; wherein at least one of R 1 to R 6 is an electron withdrawing group, and in R 1 to R 6 At least one of them is an amine group; and all or a part of the hydrogen atom of the above amine group may be substituted with an alkyl group having 1 to 6 carbon atoms; in the formula (2), R 7 to R 16 are each independently a hydrogen atom; An electron withdrawing group or an amine group; wherein at least one of R 7 to R 16 is an amine group; and all or a part of the hydrogen atom of the above amine group may be substituted by a hydrocarbon group having 1 to 6 carbon atoms; a single bond, a carbonyl group, a carbonyloxy group, a carbonylmethylene group, a sulfinyl group, a sulfonyl group, a methylene group or an alkylene group having a carbon number of 2 to 6; wherein the above methylene group and an alkylene group are hydrogen All or a portion of an atom may also be substituted by a cyano group, a halogen atom or a fluoroalkyl group.
在本發明的第1態樣中,優選著色組成物中所含有的[I]鹼溶性樹脂是包含如下結構單元的共聚物:(I-1)由選自由不飽和羧酸及不飽和羧酸酐所構成的群組的至少1種所形成的結構單元、(I-2)由含有環氧基的不飽和化合物所形成的結構單元。 In the first aspect of the invention, it is preferred that the [I] alkali-soluble resin contained in the coloring composition is a copolymer comprising the following structural unit: (I-1) is selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides. At least one structural unit formed in the group formed, and (I-2) a structural unit formed of an epoxy group-containing unsaturated compound.
在本發明的第1態樣中,優選著色圖案是在200℃以下的硬化溫度下所形成的著色圖案。 In the first aspect of the invention, it is preferable that the colored pattern is a colored pattern formed at a curing temperature of 200 ° C or lower.
在本發明的第1態樣中,優選於著色圖案上包含保護膜,所述保護膜由含有如下化合物的感放射線性樹脂組成物而形成:[A]具有環氧基的化合物、[B]具有乙烯性不飽和鍵的聚合性化合物、[C]感放射線性聚合起始劑、以及[D]選自由上述式(1)所表示的化合物及上述式(2)所表示的化合物所構成的群組的至少1種化合物。 In a first aspect of the invention, it is preferable that a protective film is formed on the colored pattern, and the protective film is formed of a radiation-sensitive resin composition containing a compound: [A] a compound having an epoxy group, [B] a polymerizable compound having an ethylenically unsaturated bond, [C] a radiation-sensitive polymerization initiator, and [D] selected from the group consisting of the compound represented by the above formula (1) and the compound represented by the above formula (2) At least one compound of the group.
在本發明的第1態樣中,優選感放射線性樹脂組成物中所含有的[A]具有環氧基的化合物是聚合物。 In the first aspect of the invention, it is preferred that the compound having an epoxy group contained in the radiation-sensitive resin composition of [A] is a polymer.
在本發明的第1態樣中,優選感放射線性樹脂組成物中所含有的[A]具有環氧基的化合物進一步具有羧基。 In the first aspect of the invention, it is preferable that the compound having an epoxy group contained in the radiation-sensitive resin composition of [A] further has a carboxyl group.
在本發明的第1態樣中,優選保護膜是在200℃以下的硬化溫度下所形成的保護膜。 In the first aspect of the invention, it is preferable that the protective film is a protective film formed at a curing temperature of 200 ° C or lower.
在本發明的第1態樣中,優選著色圖案是在比保護膜的硬化溫度更低的硬化溫度下所形成的著色圖案。 In the first aspect of the invention, it is preferable that the colored pattern is a colored pattern formed at a curing temperature lower than a curing temperature of the protective film.
本發明的第2態樣涉及一種液晶顯示元件,其特徵在 於包含本發明的第1態樣的彩色濾光片。 A second aspect of the invention relates to a liquid crystal display element characterized in A color filter comprising the first aspect of the invention.
本發明的第3態樣涉及一種彩色濾光片的製造方法,其特徵在於包括如下步驟:[1]在基板上形成著色組成物的塗膜的步驟,所述著色組成物含有選自由二酮基吡咯並吡咯類顏料、鹵化鋅酞菁類顏料、三芳基甲烷類染料及偶氮類染料所構成的群組的至少1種著色劑;[2]在所述著色組成物的塗膜上形成著色圖案的步驟;[3]在200℃以下對所述形成有著色圖案的塗膜進行硬化的步驟;[4]於步驟[3]的所述具有經硬化的塗膜的基板上形成含有通式[a]所表示的結構單元的聚醯亞胺膜的步驟;以及[5]對所述聚醯亞胺膜照射偏光的紫外線而形成配向膜的步驟;
(通式[a]中,P1表示具有脂環族結構的4價有機基,P2表示2價有機基)。 (In the general formula [a], P 1 represents a tetravalent organic group having an alicyclic structure, and P 2 represents a divalent organic group).
在本發明的第3態樣中,優選表示聚醯亞胺所含有的
結構單元的通式[a]的P1是選自由下述結構所構成的群組的至少1種結構;
(式中,P3、P4、P5及P6分別獨立地表示氫或碳數為1~4的有機基)。 (In the formula, P 3 , P 4 , P 5 and P 6 each independently represent hydrogen or an organic group having 1 to 4 carbon atoms).
在本發明的第3態樣中,優選著色組成物進一步含有[I]鹼溶性樹脂、[II]具有乙烯性不飽和鍵的聚合性化合物及[III]感放射線性聚合起始劑。 In the third aspect of the invention, it is preferable that the coloring composition further contains [I] an alkali-soluble resin, [II] a polymerizable compound having an ethylenically unsaturated bond, and [III] a radiation-sensitive polymerization initiator.
在本發明的第3態樣中,優選著色組成物含有選自由下述式(1)所表示的化合物、下述式(2)所表示的化合物、三級胺化合物、胺鹽、鏻鹽、脒鹽、醯胺化合物、硫醇化合物、嵌段異氰酸酯化合物及含有咪唑環的化合物所構成的群組的至少1種化合物;[化7]
(式(1)中,R1~R6分別獨立為氫原子、吸電子基或胺基;其中,R1~R6中的至少1個是吸電子基,且R1~R6中的至少1個是胺基;而且,上述胺基的氫原子的全部或一部分也可以被碳數為1~6的烷基取代;式(2)中,R7~R16分別獨立為氫原子、吸電子基或胺基;其中,R7~R16中的至少1個是胺基;而且,上述胺基的氫原子的全部或一部分也可以被碳數為1~6的烴基取代;A為單鍵、羰基、羰氧基、羰基亞甲基、亞磺醯基、磺醯基、亞甲基或碳數為2~6的伸烷基;其中,上述亞甲基及伸烷基的氫原子的全部或一部分也可以被氰基、鹵素原子或氟烷基取代)。 (In the formula (1), R 1 to R 6 are each independently a hydrogen atom, an electron withdrawing group or an amine group; wherein at least one of R 1 to R 6 is an electron withdrawing group, and in R 1 to R 6 At least one of them is an amine group; and all or a part of the hydrogen atom of the above amine group may be substituted with an alkyl group having 1 to 6 carbon atoms; in the formula (2), R 7 to R 16 are each independently a hydrogen atom; An electron withdrawing group or an amine group; wherein at least one of R 7 to R 16 is an amine group; and all or a part of the hydrogen atom of the above amine group may be substituted by a hydrocarbon group having 1 to 6 carbon atoms; a single bond, a carbonyl group, a carbonyloxy group, a carbonylmethylene group, a sulfinyl group, a sulfonyl group, a methylene group or an alkylene group having a carbon number of 2 to 6; wherein the above methylene group and an alkylene group are hydrogen All or a portion of an atom may also be substituted by a cyano group, a halogen atom or a fluoroalkyl group.
在本發明的第3態樣中,優選在步驟[3]與步驟[4]之間包含如下步驟:[x]於基板上形成感放射線性樹脂組成物的塗膜的步驟,所述感放射線性樹脂組成物含有:[A]具有環氧基的化合物、[B]具有乙烯性不飽和鍵的聚合性化合物、[C]感放射線性聚合起始劑、及[D]選自由上述式(1)所表示的化合物及上述式(2)所表示的化合物所構成的群組的至少1種化合物;[xi]對感放射線性樹脂組成物的塗膜的至少一部分照射放射線的步驟;[xii]對步驟[xi]中照射了放射線的塗膜進行顯影的步驟;以及[xiii]在200℃以下使步驟[xii]中進行了顯影的塗膜硬化的步驟。 In a third aspect of the invention, preferably, the step of [3] and the step [4] includes the step of: [x] forming a coating film of the radiation-sensitive resin composition on the substrate, the radiation. The resin composition contains: [A] a compound having an epoxy group, [B] a polymerizable compound having an ethylenically unsaturated bond, [C] a radiation-sensitive polymerization initiator, and [D] selected from the above formula ( 1) at least one compound of the group consisting of the compound represented by the above formula (2); [xi] a step of irradiating at least a part of the coating film of the radiation sensitive resin composition; [xii a step of developing a coating film irradiated with radiation in the step [xi]; and [xiii] a step of hardening the coating film developed in the step [xii] at 200 ° C or lower.
在本發明的第3態樣中,優選步驟[3]的硬化溫度是比步驟[xiii]的硬化溫度更低的溫度。 In the third aspect of the invention, it is preferred that the hardening temperature of the step [3] is a temperature lower than the hardening temperature of the step [xiii].
根據本發明而提供可通過低溫硬化而製造且具有高可靠性的彩色濾光片及其製造方法。 According to the present invention, a color filter which can be manufactured by low-temperature hardening and which has high reliability and a method of manufacturing the same are provided.
而且,根據本發明而提供包含通過低溫硬化而製造的具有高可靠性的彩色濾光片,顯示品質優異的液晶顯示元件。 Further, according to the present invention, a liquid crystal display element comprising a color filter having high reliability which is produced by low-temperature curing and having excellent display quality is provided.
以下對本發明的實施形態加以說明。 Embodiments of the present invention will be described below.
另外,在本發明中,在曝光時所照射的“放射線”是包括可見光線、紫外線、遠紫外線、X射線、帶電粒子束等的概念。 Further, in the present invention, the "radiation" irradiated at the time of exposure is a concept including visible light rays, ultraviolet rays, far ultraviolet rays, X-rays, charged particle beams, and the like.
本實施形態的液晶顯示元件是包含本實施形態的彩色濾光片的彩色液晶顯示元件。 The liquid crystal display element of the present embodiment is a color liquid crystal display element including the color filter of the present embodiment.
以下,對本實施形態的液晶顯示元件加以說明。 Hereinafter, the liquid crystal display element of the present embodiment will be described.
本實施形態的液晶顯示元件例如可以是使配置有薄膜晶體管(Thin Film Transistor,TFT)的驅動用基板、與構成本實施形態的彩色濾光片的其他基板介隔液晶層而對向的結構。另外,液晶顯示元件還可以是使用在配置有薄膜晶體管(TFT)的驅動用基板上形成後述的本實施形態的著色圖案或保護膜而構成的基板、與形成有ITO(Indium Tin Oxide,摻雜有錫的氧化銦)電極的基板,介隔液晶層而對向的結構。後者的結構具有如下的優點:可使數值孔徑明顯提高,且獲得明亮的高精細的液晶顯示元件。 The liquid crystal display device of the present embodiment may be configured such that a driving substrate on which a thin film transistor (TFT) is disposed and a other substrate constituting the color filter of the present embodiment are opposed to each other by a liquid crystal layer. In addition, the liquid crystal display element may be formed by forming a coloring pattern or a protective film of the present embodiment to be described later on a driving substrate on which a thin film transistor (TFT) is disposed, and forming ITO (Indium Tin Oxide, doping). The substrate of the tin-doped indium oxide electrode, which is opposed to the liquid crystal layer. The latter structure has the advantage that the numerical aperture can be significantly improved, and a bright high-definition liquid crystal display element can be obtained.
圖1是本實施形態的彩色濾光片的模式剖面圖。 Fig. 1 is a schematic cross-sectional view showing a color filter of the embodiment.
圖1中所示的彩色濾光片10是本實施形態的彩色濾光片的一例。具有如下的結構:在透明的基板5上配置有紅色(R)、綠色(G)及藍色(B)的著色圖案6、黑色矩陣7、設於著色圖案6上的ITO電極4、設於ITO電極4上的配向膜12。另外,著色圖案6的顏色並不限定於上述RGB 3色,還可以選擇其他顏色或者進一步加入黃色 (Y)而製成4色的著色圖案。 The color filter 10 shown in Fig. 1 is an example of the color filter of the present embodiment. A configuration in which a red (R), green (G), and blue (B) colored pattern 6 , a black matrix 7 , and an ITO electrode 4 provided on the colored pattern 6 are disposed on a transparent substrate 5 The alignment film 12 on the ITO electrode 4. In addition, the color of the colored pattern 6 is not limited to the above RGB 3 colors, and other colors may be selected or yellow may be further added. (Y) is made into a four-color coloring pattern.
如後所述那樣,在本實施形態的彩色濾光片10中,著色圖案6含有適宜的著色劑而構成。具體而言,將含有優選的著色劑(包含染料等)的著色組成物塗布於基板上並進行圖案化後,使其硬化而形成。著色組成物可如後所述地製成含有感放射線性樹脂的樹脂組成物,具有可通過200℃以下的低溫硬化而形成著色圖案的特徵。因此,即使在著色劑中包含染料的情況下,亦可回避在形成著色圖案6時造成染料暴露於高溫下的現象。 As will be described later, in the color filter 10 of the present embodiment, the colored pattern 6 is formed by containing a suitable coloring agent. Specifically, a colored composition containing a preferred color former (including a dye or the like) is applied onto a substrate, patterned, and then cured. The colored composition can be formed into a resin composition containing a radiation sensitive resin as described later, and has a feature that a colored pattern can be formed by low temperature curing at 200 ° C or lower. Therefore, even in the case where the dye is contained in the coloring agent, the phenomenon that the dye is exposed to a high temperature when the colored pattern 6 is formed can be avoided.
本實施形態的彩色濾光片10的配向膜12是化學性穩定且耐熱性優異的聚醯亞胺的配向膜。而且,配向膜12是實施利用光分解型光配向技術的配向處理而形成的。光分解型光配向技術是對包含聚醯亞胺的配向膜12照射偏光紫外線,於配向膜12中各向異性地產生光分解反應,於膜中導入各向異性。該光配向技術可應用於自先前起所使用的聚醯亞胺膜中,因此是更優選的光配向技術。而且,於本實施形態的彩色濾光片10中,聚醯亞胺如後所述那樣選擇低極性結構的聚醯亞胺。因此,即使自包含染料的著色圖案6中擴散高極性的雜質,亦可抑制該些雜質吸附於配向膜12上。 The alignment film 12 of the color filter 10 of the present embodiment is an alignment film of polyimide which is chemically stable and excellent in heat resistance. Further, the alignment film 12 is formed by performing an alignment process using a photodegradable photoalignment technique. In the photodegradation type optical alignment technique, the alignment film 12 containing the polyimide is irradiated with polarized ultraviolet rays, and an optical decomposition reaction is anisotropically generated in the alignment film 12, and anisotropy is introduced into the film. This photoalignment technique can be applied to a polyimide film used from the past, and thus is a more preferable photoalignment technique. Further, in the color filter 10 of the present embodiment, the polyimine of the low-polar structure is selected as described later. Therefore, even if impurities of high polarity are diffused from the coloring pattern 6 containing the dye, adsorption of the impurities onto the alignment film 12 can be suppressed.
本實施形態的液晶顯示元件的彩色濾光片可於著色圖案6上設置保護膜。 The color filter of the liquid crystal display element of this embodiment can provide a protective film on the coloring pattern 6.
圖2是本實施形態的彩色濾光片的其他例的模式剖面圖。 Fig. 2 is a schematic cross-sectional view showing another example of the color filter of the embodiment.
圖2中所示的彩色濾光片20是本實施形態的彩色濾光片的其他例,與上述本實施形態的彩色濾光片10相比而言,除了於ITO電極上具有保護膜以外,具有同樣的結構。因此,關於與彩色濾光片10共用的構成元件,使用同一符號加以說明,省略重複說明。 The color filter 20 shown in FIG. 2 is another example of the color filter of the present embodiment, and the color filter 10 of the present embodiment has a protective film in addition to the ITO electrode. Have the same structure. Therefore, the constituent elements that are common to the color filter 10 will be described using the same reference numerals, and the description thereof will not be repeated.
彩色濾光片20具有如下的結構:於透明基板5上配置有紅色(R)、綠色(G)及藍色(B)的著色圖案6、黑色矩陣7、設於著色圖案6上的保護膜8、設於保護膜8上的ITO電極4、設於ITO電極4上的配向膜12。另外,如上所述,著色圖案6的顏色並不限定於上述RGB 3色,還可以選擇其他顏色或者進一步加入黃色(Y)而製成4色的著色圖案。 The color filter 20 has a structure in which a red (R), green (G), and blue (B) colored pattern 6 , a black matrix 7 , and a protective film provided on the colored pattern 6 are disposed on the transparent substrate 5 . 8. An ITO electrode 4 provided on the protective film 8, and an alignment film 12 provided on the ITO electrode 4. Further, as described above, the color of the colored pattern 6 is not limited to the above-described RGB three colors, and other colors may be selected or yellow (Y) may be further added to form a four-color colored pattern.
在本實施形態的彩色濾光片20中,著色圖案6含有適宜的著色劑(包含染料等)而構成。具體而言,將含有染料等著色劑的著色組成物塗布於基板5上而進行圖案化後,於200℃以下的低溫下進行硬化而形成。 In the color filter 20 of the present embodiment, the colored pattern 6 is composed of a suitable coloring agent (including a dye or the like). Specifically, a colored composition containing a coloring agent such as a dye is applied onto the substrate 5 to be patterned, and then cured at a low temperature of 200° C. or lower.
本實施形態的彩色濾光片20的保護膜8為了實現電氣特性或可靠性等優異的ITO電極4而配設於著色圖案6上。保護膜8對著色圖案6進行覆蓋。因此,保護膜8發揮如下的功能:於後述的配向膜12的光配向處理中,自紫外線照射保護著色圖案6中所含的染料。另外,於著色圖案中的染料中發生分解而產生高極性的雜質時,發揮如下的功能:抑制該雜質自著色圖案6向液晶顯示元件的內部擴散。 The protective film 8 of the color filter 20 of the present embodiment is disposed on the colored pattern 6 in order to realize the ITO electrode 4 excellent in electrical characteristics and reliability. The protective film 8 covers the colored pattern 6. Therefore, the protective film 8 functions to protect the dye contained in the colored pattern 6 from ultraviolet rays during the photoalignment treatment of the alignment film 12 to be described later. Further, when the dye in the colored pattern is decomposed to generate a highly polar impurity, the function of suppressing the diffusion of the impurity from the colored pattern 6 into the inside of the liquid crystal display element is exhibited.
此時,保護膜8與著色圖案6同樣地塗布感放射線性的樹脂組成物而進行圖案化後,加以硬化而形成。而且,保護膜8形成用感放射線性樹脂組成物(以下略稱為感放射線性樹脂組成物)如後述那樣可設為使用與該著色組成物同系的類似材料的樹脂組成物。該些組成物均具有可通過200℃以下的低溫硬化而分別形成著色圖案6與保護膜8的特徵。 At this time, the protective film 8 is formed by applying a radiation-sensitive resin composition in the same manner as the coloring pattern 6 and patterning it, followed by curing. In addition, the radiation-sensitive resin composition for forming a protective film 8 (hereinafter, abbreviated as a radiation-sensitive resin composition) can be a resin composition using a similar material similar to the coloring composition as will be described later. Each of these compositions has a feature that the colored pattern 6 and the protective film 8 can be formed by low-temperature curing at 200 ° C or lower.
因此,於本實施形態的彩色濾光片20中,變得可通過200℃以下的低溫硬化而分別形成著色圖案6與保護膜8。本實施形態的彩色濾光片20可利用低溫硬化而製造。 Therefore, in the color filter 20 of the present embodiment, the colored pattern 6 and the protective film 8 can be formed by low-temperature curing at 200 ° C or lower. The color filter 20 of the present embodiment can be produced by low-temperature curing.
而且,於彩色濾光片20中,可利用200℃以下的低溫硬化而形成保護膜8,因此先前所形成的著色圖案6變得並不暴露於用以形成保護膜8的高溫加熱的狀態下。因此,於彩色濾光片20中,於形成著色圖案6時,即使使用於耐熱性方面具有課題的染料作為著色劑,亦可減低步驟劣化。亦即,於彩色濾光片20中,變得可選擇染料作為著色組成物的著色劑,且變得可由使用染料的著色組成物而形成顏色特性優異的著色圖案6。 Further, in the color filter 20, the protective film 8 can be formed by low-temperature curing at 200 ° C or lower, so that the previously formed colored pattern 6 becomes not exposed to the high-temperature heating for forming the protective film 8 . Therefore, in the color filter 20, when the colored pattern 6 is formed, even if a dye having a problem in heat resistance is used as a coloring agent, the step deterioration can be reduced. In other words, in the color filter 20, the dye can be selected as a coloring agent of the coloring composition, and the coloring pattern 6 excellent in color characteristics can be formed by using the coloring composition of the dye.
另外,如上所述,著色組成物、感放射線性樹脂組成物可以均設為使用同系的類似材料的感放射線性樹脂組成物。而且,分別用於製造彩色濾光片20。因此,於製造彩色濾光片20時,可以考慮在著色圖案6上形成保護膜8而調整形成著色圖案6時的硬化溫度。亦即,在基板5上,利用與單獨形成著色圖案6時最適宜的硬化溫度相比而言 更低的硬化溫度而形成著色圖案6。其後,可通過對著色圖案6上所形成的保護膜8進行硬化加熱而進行對著色圖案6的加熱。 Further, as described above, the coloring composition and the radiation sensitive resin composition may each be a radiation sensitive resin composition using a similar material of the same type. Moreover, they are used to manufacture the color filter 20, respectively. Therefore, when manufacturing the color filter 20, it is conceivable to form the protective film 8 on the colored pattern 6 to adjust the hardening temperature at the time of forming the colored pattern 6. That is, on the substrate 5, compared with the most suitable hardening temperature when the colored pattern 6 is separately formed. The colored pattern 6 is formed at a lower hardening temperature. Thereafter, the colored pattern 6 can be heated by hardening and heating the protective film 8 formed on the colored pattern 6.
例如,在著色圖案6與保護膜8的最適宜的硬化溫度分別為200℃以下,具體而言為180℃的情況下,可以用150℃的硬化溫度而預先在基板5上形成著色圖案6。其次,在該著色圖案6上形成感放射線性樹脂組成物的塗膜,在最適宜的180℃下進行硬化,由此而形成保護膜8。在這種情況下,並且變得可進行對處於其下層的著色圖案6的加熱,獲得所期望的狀態的著色圖案6。其結果,可選擇染料作為著色組成物的著色劑,利用由使用染料的著色組成物而形成的著色圖案6,可提供顏色特性優異的彩色濾光片20。 For example, in the case where the optimum curing temperature of the colored pattern 6 and the protective film 8 is 200 ° C or lower, specifically, 180 ° C, the colored pattern 6 can be formed on the substrate 5 in advance with a curing temperature of 150 ° C. Next, a coating film of a radiation-sensitive resin composition is formed on the colored pattern 6, and is cured at an optimum temperature of 180 ° C to form a protective film 8. In this case, and it becomes possible to perform heating of the coloring pattern 6 in the lower layer thereof, the coloring pattern 6 of the desired state is obtained. As a result, a dye can be selected as the coloring agent of the coloring composition, and the coloring pattern 6 formed by using the coloring composition of the dye can provide the color filter 20 excellent in color characteristics.
而且,於本實施形態的彩色濾光片20中,於保護膜8上形成ITO電極4後,於ITO電極4上形成液晶配向控制用配向膜12。配向膜12是化學性穩定且耐熱性優異的包含聚醯亞胺的配向膜,是實施上述的利用光分解型光配向處理法的配向處理而形成。而且,於本實施形態的彩色濾光片20中,聚醯亞胺可選擇滿足耐熱性或電氣特性的低極性結構的聚醯亞胺。因此,即使存在自包含染料的著色圖案6擴散高極性雜質的現象,亦可抑制該些雜質吸附於配向膜12上。而且,可抑制液晶顯示元件的顯示品質降低。 Further, in the color filter 20 of the present embodiment, after the ITO electrode 4 is formed on the protective film 8, the alignment film 12 for liquid crystal alignment control is formed on the ITO electrode 4. The alignment film 12 is an alignment film containing polyimide which is chemically stable and excellent in heat resistance, and is formed by performing the above-described alignment treatment by a photodegradable photoalignment treatment method. Further, in the color filter 20 of the present embodiment, the polyimide may be selected from a polyimide having a low polarity structure which satisfies heat resistance or electrical properties. Therefore, even if there is a phenomenon in which the coloring pattern 6 containing the dye diffuses highly polar impurities, the impurities can be suppressed from being adsorbed on the alignment film 12. Further, it is possible to suppress deterioration in display quality of the liquid crystal display element.
其次,對應用以上所說明的本實施形態的彩色濾光片的本實施形態的液晶顯示元件的結構加以說明。 Next, the configuration of the liquid crystal display element of this embodiment to which the color filter of the present embodiment described above is applied will be described.
圖3是包含本實施形態的彩色濾光片的液晶顯示元件的模式剖面圖。 Fig. 3 is a schematic cross-sectional view showing a liquid crystal display element including the color filter of the embodiment.
圖3中所示的液晶顯示元件1是本實施形態的液晶顯示元件的一例,是TFT驅動的扭轉向列(Twisted Nematic,TN)型液晶模式的液晶顯示元件。該液晶顯示元件1具有如下的結構:驅動用基板與圖2所示的構成本實施形態的彩色濾光片20的基板介隔包含TN液晶的液晶13而對向的結構。另外,於本實施形態中,亦可使用構成圖1所示的彩色濾光片10的基板,使其他結構與液晶顯示元件1相同,從而構成本實施形態的液晶顯示元件的其他例。 The liquid crystal display element 1 shown in FIG. 3 is an example of a liquid crystal display element of the present embodiment, and is a TFT-driven twisted nematic (TN) liquid crystal mode liquid crystal display element. The liquid crystal display element 1 has a structure in which a driving substrate and a substrate constituting the color filter 20 of the present embodiment shown in FIG. 2 are opposed to each other by a liquid crystal 13 containing TN liquid crystal. Further, in the present embodiment, a substrate constituting the color filter 10 shown in FIG. 1 may be used, and other configurations may be the same as those of the liquid crystal display element 1 to constitute another example of the liquid crystal display element of the present embodiment.
如圖3所示,在液晶顯示元件1的透明的基板2的與液晶13相接之側,將包含ITO的透明的像素電極3與TFT(未圖示)配設為格子狀而構成驅動用基板。而且,在透明的基板5的與液晶13相接之側,配置有上述的通過低溫硬化而製造的著色圖案6等,構成彩色濾光片20。具體而言於基板5上配設如下元件而構成彩色濾光片20:在與像素電極3對向的位置所設的紅色、綠色及藍色的著色圖案6,黑色矩陣7,在著色圖案6上所設的保護膜8,在保護膜8上所設的ITO電極4,在ITO電極4上所設的配向膜12。ITO電極4在液晶顯示元件1中構成公共電極。 As shown in FIG. 3, on the side of the transparent substrate 2 of the liquid crystal display element 1 that is in contact with the liquid crystal 13, the transparent pixel electrode 3 including ITO and the TFT (not shown) are arranged in a lattice shape to constitute a driving. Substrate. Further, on the side of the transparent substrate 5 that is in contact with the liquid crystal 13, the above-described colored pattern 6 or the like which is produced by low-temperature curing is disposed to constitute the color filter 20. Specifically, the color filter 20 is formed on the substrate 5 by the following elements: a red, green, and blue coloring pattern 6 provided at a position facing the pixel electrode 3, and a black matrix 7 in the coloring pattern 6 The protective film 8 provided above, the ITO electrode 4 provided on the protective film 8, and the alignment film 12 provided on the ITO electrode 4. The ITO electrode 4 constitutes a common electrode in the liquid crystal display element 1.
於液晶顯示元件1中,在基板2上設有與基板5同樣的配向膜12。各個配向膜12包含滿足耐熱性或電氣特性的低極性結構的聚醯亞胺。而且,實施了照射偏光紫外線的光配向處理,實現於基板2與基板5之間所夾持的液晶 13的均一配向。配向膜12包含低極性結構的聚醯亞胺,即使存在自著色圖案6擴散高極性雜質的現象,亦可抑制該些雜質吸附於配向膜12上。而且,可抑制液晶顯示元件1的顯示品質降低。 In the liquid crystal display element 1, the alignment film 12 similar to the substrate 5 is provided on the substrate 2. Each of the alignment films 12 contains a polyimine having a low polarity structure satisfying heat resistance or electrical properties. Further, the light alignment treatment of the polarized ultraviolet light is performed to realize the liquid crystal sandwiched between the substrate 2 and the substrate 5. 13 uniform orientation. The alignment film 12 contains a polyimine having a low polarity structure, and even if a phenomenon of diffusing highly polar impurities from the colored pattern 6 exists, adsorption of the impurities on the alignment film 12 can be suppressed. Moreover, the deterioration of the display quality of the liquid crystal display element 1 can be suppressed.
在基板2與基板5中,在與液晶13相接之側的相反側分別配置有偏光板14。基板2與基板5的間隔通常為2 μm~10 μm,該些元件通過設在周邊部的密封材料16而相互固定。 In the substrate 2 and the substrate 5, a polarizing plate 14 is disposed on the side opposite to the side in contact with the liquid crystal 13, respectively. The distance between the substrate 2 and the substrate 5 is usually 2 μm to 10 μm, and these elements are fixed to each other by the sealing material 16 provided at the peripheral portion.
在圖3中,符號17是指自背光單元(未圖示)而向液晶13照射的背光源光。背光單元例如可使用組合有冷陰極螢光管(CCFL:Cold Cathode Fluorescent Lamp)等螢光管與散射板而成的結構的背光單元。而且,還可以使用以白色LED為光源的背光單元。白色LED例如可列舉:使用具有獨立光譜的紅色LED、綠色LED、藍色LED而獲得白色光的白色LED,將紅色LED、綠色LED、藍色LED加以組合而通過混色獲得白色光的白色LED,將藍色LED、紅色LED、綠色螢光體加以組合而通過混色獲得白色光的白色LED,將藍色LED、紅色發光螢光體、綠色發光螢光體加以組合而通過混色獲得白色光的白色LED,通過藍色LED與YAG類螢光體的混色而獲得白色光的白色LED,將藍色LED、橙色發光螢光體、綠色發光螢光體加以組合而通過混色獲得白色光的白色LED,將紫外線LED、紅色發光螢光體、綠色發光螢光體、藍色發光螢光體加以組合而通過混色獲得白色光的白色LED等。 In FIG. 3, reference numeral 17 denotes backlight light that is irradiated to the liquid crystal 13 from a backlight unit (not shown). As the backlight unit, for example, a backlight unit having a structure in which a fluorescent tube such as a Cold Cathode Fluorescent Lamp (CCFL) and a diffusion plate are combined can be used. Moreover, a backlight unit using a white LED as a light source can also be used. Examples of the white LED include a white LED that obtains white light using a red LED having an independent spectrum, a green LED, and a blue LED, and a white LED that combines a red LED, a green LED, and a blue LED to obtain white light by color mixing. A white LED that combines a blue LED, a red LED, and a green phosphor to obtain white light by color mixing, and combines a blue LED, a red luminescent phosphor, and a green luminescent phosphor to obtain a white white by color mixing. The LED obtains a white LED of white light by color mixing of a blue LED and a YAG-based phosphor, and combines a blue LED, an orange-emitting phosphor, and a green-emitting phosphor to obtain a white LED of white light by color mixing. A white LED or the like which combines an ultraviolet LED, a red luminescent phosphor, a green luminescent phosphor, and a blue luminescent phosphor to obtain white light by color mixing.
於本實施形態的液晶顯示元件中,除了上述TN型以外,還可以設為超扭轉向列(Super Twisted Nematic,STN)型、共面切換(In-Planes Switching,IPS)型、垂直配向(Vertical Alignment,VA)型或光學補償雙折射(Optically Compensated Birefringence,OCB)型等液晶模式。在這種情況下,液晶配向用配向膜選擇在各液晶模式中顯示最適宜的配向特性的配向膜,例如在VA型的情況下使用垂直配向型的配向膜。 In addition to the TN type, the liquid crystal display device of the present embodiment may be a Super Twisted Nematic (STN) type, an In-Planes Switching (IPS) type, or a vertical alignment (Vertical). Liquid crystal mode such as Alignment, VA) or Optically Compensated Birefringence (OCB) type. In this case, the alignment film for liquid crystal alignment selects an alignment film which exhibits optimum alignment characteristics in each liquid crystal mode, and for example, in the case of the VA type, a vertical alignment type alignment film is used.
本實施形態的液晶顯示元件是具有以上結構,其次對其主要構成元件的本實施形態的彩色濾光片加以更詳細的說明。特別是對構成本實施形態的彩色濾光片的各構成構件加以詳細說明。 The liquid crystal display element of the present embodiment has the above configuration, and the color filter of the present embodiment which is the main constituent element will be described in more detail. In particular, each constituent member constituting the color filter of the present embodiment will be described in detail.
本實施形態的彩色濾光片如上所述那樣包含:著色圖案、於著色圖案上的ITO電極上所配置的配向膜。可於該著色圖案上配設保護膜。而且,本實施形態的彩色濾光片是顏色特性優異、且可通過低溫硬化而製造的彩色濾光片。 As described above, the color filter of the present embodiment includes a colored pattern and an alignment film disposed on the ITO electrode on the colored pattern. A protective film may be disposed on the colored pattern. Further, the color filter of the present embodiment is a color filter which is excellent in color characteristics and can be produced by low-temperature curing.
作為著色圖案,可使用著色組成物而形成於適當的基板上。作為配向膜,可使用液晶配向劑而於基板上形成低極性結構的聚醯亞胺膜,實施光配向處理而形成。保護膜可使用感放射線性樹脂組成物而形成於著色圖案上。因此,本實施形態的彩色濾光片可使用本實施形態的著色組成物、感放射線性樹脂組成物及液晶配向劑而構成。 As the colored pattern, a colored composition can be used to form a suitable substrate. As the alignment film, a polyimide film having a low polarity structure is formed on a substrate by using a liquid crystal alignment agent, and a photoalignment treatment is performed. The protective film can be formed on the colored pattern using a radiation sensitive resin composition. Therefore, the color filter of the present embodiment can be configured by using the coloring composition, the radiation sensitive resin composition, and the liquid crystal alignment agent of the present embodiment.
以下,首先對本實施形態的彩色濾光片的著色圖案,特別是形成該著色圖案的本實施形態的著色組成物加以說 明。 Hereinafter, first, the coloring pattern of the color filter of the present embodiment, in particular, the coloring composition of the embodiment in which the coloring pattern is formed will be described. Bright.
本實施形態的彩色濾光片的著色圖案可使用本實施形態的著色組成物而形成。 The coloring pattern of the color filter of the present embodiment can be formed using the coloring composition of the present embodiment.
本實施形態的彩色濾光片的製造中所使用的著色組成物含有[I]鹼溶性樹脂、[II]聚合性化合物、[III]聚合起始劑、及[IV]著色劑。而且,可進一步含有[V]化合物。而且,只要不損及本發明的效果,則還可以含有其他任意成分。以下,對著色組成物中所含有的各成分加以說明。 The colored composition used in the production of the color filter of the present embodiment contains [I] an alkali-soluble resin, a [II] polymerizable compound, a [III] polymerization initiator, and a [IV] colorant. Further, a compound of [V] may be further contained. Further, other optional components may be contained as long as the effects of the present invention are not impaired. Hereinafter, each component contained in the coloring composition will be described.
[I]鹼溶性樹脂若為具有羧基而具有鹼顯影性的樹脂,則並無特別限定。而且,優選包含選自由具有(甲基)丙烯醯氧基的結構單元及具有環氧基的結構單元所構成的群組的至少1種結構單元的共聚物。[I]鹼溶性樹脂具有上述特定結構單元,因此可形成具有優異的表面硬化性及深部硬化性的硬化膜。 [I] The alkali-soluble resin is not particularly limited as long as it has a carboxyl group and has alkali developability. Further, a copolymer comprising at least one structural unit selected from the group consisting of a structural unit having a (meth)acryloxy group and a structural unit having an epoxy group is preferable. [I] The alkali-soluble resin has the specific structural unit described above, and thus a cured film having excellent surface hardenability and deep-curing property can be formed.
[I]鹼溶性樹脂可通過使如下的結構單元共聚而合成,從而獲得包含該些結構單元的共聚物:(I-1)由選自由不飽和羧酸及不飽和羧酸酐所構成的群組的至少1種(以下亦稱為“(I-1)化合物”)所形成的結構單元、(I-2)由含有環氧基的不飽和化合物(以下亦稱為“(I-2)化合物”)所形成的結構單元。 [I] an alkali-soluble resin can be synthesized by copolymerizing a structural unit to obtain a copolymer comprising the structural unit: (I-1) is selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic anhydride. At least one structural unit (hereinafter also referred to as "(I-1) compound")), (I-2) is an unsaturated compound containing an epoxy group (hereinafter also referred to as "(I-2) compound) ") The structural unit formed.
[I]鹼溶性樹脂例如可以通過在溶劑中、聚合起始劑的存在下使賦予含有羧基的結構單元的(I-1)化合物與賦予 含有環氧基的結構單元的(I-2)化合物共聚而製造。而且,還可以進一步添加(I-3)賦予含有羥基的結構單元的含羥基不飽和化合物(以下亦稱為“(I-3)化合物”)而製成共聚物。另外,在[I]鹼溶性樹脂的製造中,還可以與上述(I-1)化合物、(I-2)化合物及(I-3)化合物一同進一步添加(I-4)化合物(賦予源自上述(I-1)化合物、(I-2)化合物及(I-3)化合物的結構單元以外的結構單元的不飽和化合物)而製成共聚物。以下,對各化合物加以詳述。 [I] an alkali-soluble resin can be imparted to a compound (I-1) which imparts a structural unit containing a carboxyl group in the presence of a polymerization initiator in a solvent, for example. The compound of the formula (I-2) containing an epoxy group-containing structural unit is copolymerized and produced. Further, (I-3) a hydroxyl group-containing unsaturated compound (hereinafter also referred to as "(I-3) compound")) to which a structural unit containing a hydroxyl group is added may be further added to form a copolymer. Further, in the production of the [I] alkali-soluble resin, the compound (I-4) may be further added together with the compound (I-1), the compound (I-2) and the compound (I-3). The (I-1) compound, the (I-2) compound, and the unsaturated compound of the structural unit other than the structural unit of the (I-3) compound are used to form a copolymer. Hereinafter, each compound will be described in detail.
(I-1)化合物可列舉不飽和單羧酸、不飽和二羧酸、不飽和二羧酸的酸酐、多元羧酸的單[(甲基)丙烯醯氧基烷基]酯、在兩末端具有羧基與羥基的聚合物的單(甲基)丙烯酸酯、具有羧基的不飽和多環式化合物及其酸酐等。 Examples of the compound (I-1) include an unsaturated monocarboxylic acid, an unsaturated dicarboxylic acid, an acid anhydride of an unsaturated dicarboxylic acid, and a mono[(meth)acryloxyalkylalkyl] ester of a polyvalent carboxylic acid at both ends. A mono(meth)acrylate having a polymer having a carboxyl group and a hydroxyl group, an unsaturated polycyclic compound having a carboxyl group, an acid anhydride thereof, and the like.
不飽和單羧酸例如可列舉丙烯酸、甲基丙烯酸、丁烯酸等;不飽和二羧酸例如可列舉馬來酸、富馬酸、檸康酸、中康酸、衣康酸等;不飽和二羧酸的酸酐例如可列舉作為上述二羧酸而例示的化合物的酸酐等;多元羧酸的單[(甲基)丙烯醯氧基烷基]酯例如可列舉琥珀酸單[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]酯等;在兩末端具有羧基與羥基的聚合物的單(甲基)丙烯酸酯例如可列舉ω-羧基聚己內酯單(甲基)丙烯酸酯等; 具有羧基的不飽和多環式化合物及其酸酐例如可列舉: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-5-乙基雙環[2.2.1]庚-2-烯、5-羧基-6-甲基雙環[2.2.1]庚-2-烯、5-羧基-6-乙基雙環[2.2.1]庚-2-烯、5,6-二羧基雙環[2.2.1]庚-2-烯酸酐等。 Examples of the unsaturated monocarboxylic acid include acrylic acid, methacrylic acid, and crotonic acid; and examples of the unsaturated dicarboxylic acid include maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, and the like; Examples of the acid anhydride of the dicarboxylic acid include an acid anhydride of a compound exemplified as the above dicarboxylic acid; and a mono[(meth)acryloxyalkylalkyl] ester of a polyvalent carboxylic acid, for example, succinic acid mono [2-(A) Alkenyloxyethyl]ester, mono[2-(methyl)propenyloxyethyl] phthalate, etc.; mono(meth)acrylic acid having a polymer having a carboxyl group and a hydroxyl group at both ends Examples of the ester include ω-carboxypolycaprolactone mono(meth)acrylate; Examples of the unsaturated polycyclic compound having a carboxyl group and an acid anhydride thereof include 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, and 5 -carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2 .1] hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, and the like.
在該些(I-1)化合物中,優選單羧酸、二羧酸酐、丙烯酸、甲基丙烯酸、馬來酸酐,自共聚反應性、對於鹼性水溶液的溶解性及獲得容易性考慮,更優選丙烯酸、甲基丙烯酸、馬來酸酐。該些(I-1)化合物可單獨使用亦可將2種以上混合使用。 Among the compounds (I-1), monocarboxylic acid, dicarboxylic anhydride, acrylic acid, methacrylic acid, and maleic anhydride are preferred, and self-copolymerization reactivity, solubility in an aqueous alkaline solution, and ease of availability are more preferable. Acrylic acid, methacrylic acid, maleic anhydride. These (I-1) compounds may be used singly or in combination of two or more.
作為(I-1)化合物的使用比例,基於(I-1)化合物以及(I-2)化合物(視需要為任意的(I-3)化合物及(I-4)化合物)的合計而言,優選為5質量%~30質量%,更優選為10質量%~25質量%。通過使(I-1)化合物的使用比例為5質量%~30質量%,可使[I]鹼溶性樹脂的對於鹼性水溶液的溶解性最佳化,從而獲得放射線性感光度優異的著色組成物。 The ratio of use of the compound (I-1) is based on the total of the (I-1) compound and the (I-2) compound (optionally any of the (I-3) compound and the (I-4) compound). It is preferably 5 mass% to 30 mass%, and more preferably 10 mass% to 25% by mass. When the use ratio of the compound (I-1) is from 5% by mass to 30% by mass, the solubility of the [I] alkali-soluble resin in an aqueous alkaline solution can be optimized, and a coloring composition excellent in radiation sensitivity can be obtained. .
(I-2)化合物是具有自由基聚合性的含有環氧基的不飽和化合物。環氧基可列舉環氧乙烷基(1,2-環氧結構)、環氧丙烷基(1,3-環氧結構)。 The compound (I-2) is an epoxy group-containing unsaturated compound having a radical polymerizable property. The epoxy group may, for example, be an oxiranyl group (1,2-epoxy structure) or an propylene oxide group (1,3-epoxy structure).
具有環氧乙烷基的不飽和化合物例如可列舉丙烯酸縮水甘油酯、甲基丙烯酸縮水甘油酯、甲基丙烯酸-2-甲基 縮水甘油酯、α-乙基丙烯酸縮水甘油酯、α-正丙基丙烯酸縮水甘油酯、α-正丁基丙烯酸縮水甘油酯、丙烯酸-3,4-環氧丁基酯、甲基丙烯酸-3,4-環氧丁基酯、丙烯酸-6,7-環氧庚基酯、甲基丙烯酸-6,7-環氧庚基酯、α-乙基丙烯酸-6,7-環氧庚基酯、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、甲基丙烯酸-3,4-環氧環己基甲酯等。自使共聚反應性及著色圖案等的耐溶劑性等提高的觀點考慮,該些化合物中優選甲基丙烯酸縮水甘油酯、甲基丙烯酸-2-甲基縮水甘油酯、甲基丙烯酸-6,7-環氧庚基酯、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、甲基丙烯酸-3,4-環氧環己基酯。 Examples of the unsaturated compound having an oxiranyl group include glycidyl acrylate, glycidyl methacrylate, and -2-methyl methacrylate. Glycidyl ester, α-ethyl methacrylate, glycidyl α-n-propyl acrylate, glycidyl α-n-butyl acrylate, 3,4-epoxybutyl acrylate, methacrylic acid-3 , 4-epoxybutyl ester, acrylate-6,7-epoxyheptyl ester, -6,7-epoxyheptyl methacrylate, α-ethyl acrylate-6,7-epoxyheptyl ester , o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, methacrylic acid-3,4-epoxycyclohexylmethyl ester, and the like. From the viewpoint of improving the solvent resistance and the solvent resistance of the coloring pattern and the like, among these compounds, glycidyl methacrylate, -2-methylglycidyl methacrylate, and methacrylic acid-6, 7 are preferable. Epoxyheptyl ester, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, 3,4-epoxycyclohexyl methacrylate.
具有環氧丙烷基的不飽和化合物例如可列舉:3-(丙烯醯氧基甲基)環氧丙烷、3-(丙烯醯氧基甲基)-2-甲基環氧丙烷、3-(丙烯醯氧基甲基)-3-乙基環氧丙烷、3-(丙烯醯氧基甲基)-2-苯基環氧丙烷、3-(2-丙烯醯氧基乙基)環氧丙烷、3-(2-丙烯醯氧基乙基)-2-乙基環氧丙烷、3-(2-丙烯醯氧基乙基)-3-乙基環氧丙烷、3-(2-丙烯醯氧基乙基)-2-苯基環氧丙烷等丙烯酸酯;3-(甲基丙烯醯氧基甲基)環氧丙烷、3-(甲基丙烯醯氧基甲基)-2-甲基環氧丙烷、3-(甲基丙烯醯氧基甲基)-3-乙基環氧丙烷、3-(甲基丙烯醯氧基甲基)-2-苯基環氧丙烷、3-(2-甲基丙烯醯氧基乙基)環氧丙烷、3-(2-甲基丙烯醯氧基乙基)-2-乙基環氧丙烷、3-(2-甲基丙烯醯氧基乙基)-3-乙基環 氧丙烷、3-(2-甲基丙烯醯氧基乙基)-2-苯基環氧丙烷、3-(2-甲基丙烯醯氧基乙基)-2,2-二氟環氧丙烷等甲基丙烯酸酯等。 Examples of the unsaturated compound having an oxypropylene group include 3-(acryloxymethyl) propylene oxide, 3-(acryloxymethyl)-2-methyl propylene oxide, and 3-(propylene).醯oxymethyl)-3-ethyl propylene oxide, 3-(acryloxymethyl)-2-phenyl propylene oxide, 3-(2-propenyl methoxyethyl) propylene oxide, 3-(2-propenyloxyethyl)-2-ethyl propylene oxide, 3-(2-propenyloxyethyl)-3-ethyl propylene oxide, 3-(2-propylene oxime Acrylate such as ethyl ethyl)-2-phenyl propylene oxide; 3-(methacryloxymethyl) propylene oxide, 3-(methacryloxymethyl)-2-methyl ring Oxypropane, 3-(methacryloxymethyl)-3-ethyl propylene oxide, 3-(methacryloxymethyl)-2-phenyl propylene oxide, 3-(2- Methyl propylene methoxyethyl) propylene oxide, 3-(2-methylpropenyloxyethyl)-2-ethyl propylene oxide, 3-(2-methylpropenyloxyethyl) -3-ethyl ring Oxypropane, 3-(2-methylpropenyloxyethyl)-2-phenyl propylene oxide, 3-(2-methylpropenyloxyethyl)-2,2-difluoropropylene oxide Ethyl methacrylate and the like.
該些(I-2)化合物中優選(甲基)丙烯酸縮水甘油酯。該些(I-2)化合物可單獨使用亦可將2種以上混合使用。 Among these (I-2) compounds, glycidyl (meth)acrylate is preferred. These (I-2) compounds may be used alone or in combination of two or more.
作為(I-2)化合物的使用比例,基於(I-1)化合物以及(I-2)化合物(視需要為任意的(I-3)化合物及(I-4)化合物)的合計而言,優選為5質量%~60質量%,更優選為10質量%~50質量%。通過使(I-2)化合物的使用比例為5質量%~60質量%,可形成具有優異的硬化性等的硬化膜。 The ratio of use of the compound (I-2) is based on the total of the (I-1) compound and the (I-2) compound (optionally any of the (I-3) compound and the (I-4) compound). It is preferably 5% by mass to 60% by mass, and more preferably 10% by mass to 50% by mass. When the use ratio of the compound (I-2) is from 5% by mass to 60% by mass, a cured film having excellent curability or the like can be formed.
(I-3)化合物首先可列舉具有羥基的(甲基)丙烯酸酯、具有酚性羥基的(甲基)丙烯酸酯、羥基苯乙烯。 The (I-3) compound may first be a (meth) acrylate having a hydroxyl group, a (meth) acrylate having a phenolic hydroxyl group, or a hydroxystyrene.
具有羥基的丙烯酸酯可列舉:丙烯酸-2-羥基乙酯、丙烯酸-3-羥基丙酯、丙烯酸-4-羥基丁酯、丙烯酸-5-羥基戊酯、丙烯酸-6-羥基己酯等。 Examples of the acrylate having a hydroxyl group include 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 5-hydroxypentyl acrylate, and 6-hydroxyhexyl acrylate.
而且,具有羥基的甲基丙烯酸酯可列舉:甲基丙烯酸-2-羥基乙酯、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-5-羥基戊酯、甲基丙烯酸-6-羥基己酯等。 Further, examples of the methacrylate having a hydroxyl group include 2-hydroxyethyl methacrylate, 3-hydroxypropyl methacrylate, 4-hydroxybutyl methacrylate, and 5-hydroxyl methacrylate. Ester, -6-hydroxyhexyl methacrylate, and the like.
具有酚性羥基的丙烯酸酯可列舉:丙烯酸-2-羥基苯酯、丙烯酸-4-羥基苯酯等。具有酚性羥基的甲基丙烯酸酯可列舉甲基丙烯酸-2-羥基苯酯、甲基丙烯酸-4-羥基苯酯 等。 Examples of the acrylate having a phenolic hydroxyl group include 2-hydroxyphenyl acrylate and 4-hydroxyphenyl acrylate. Examples of the methacrylate having a phenolic hydroxyl group include 2-hydroxyphenyl methacrylate and 4-hydroxyphenyl methacrylate. Wait.
羥基苯乙烯優選為鄰羥基苯乙烯、對羥基苯乙烯、α-甲基-對羥基苯乙烯。該些(I-3)化合物可單獨使用亦可將2種以上混合使用。 The hydroxystyrene is preferably o-hydroxystyrene, p-hydroxystyrene, or α-methyl-p-hydroxystyrene. These (I-3) compounds may be used alone or in combination of two or more.
作為(I-3)化合物的使用比例,基於(I-1)化合物、(I-2)化合物以及(I-3)化合物(視需要為任意的(I-4)化合物)的合計而言,優選為1質量%~30質量%,更優選為5質量%~25質量%。 The ratio of use of the compound (I-3) is based on the total of the (I-1) compound, the (I-2) compound, and the (I-3) compound (optionally any (I-4) compound). It is preferably 1% by mass to 30% by mass, and more preferably 5% by mass to 25% by mass.
(I-4)化合物如果是上述(I-1)化合物、(I-2)化合物及(I-3)化合物以外的不飽和化合物,則並無特別限制。(I-4)化合物例如可列舉甲基丙烯酸鏈狀烷基酯,甲基丙烯酸環狀烷基酯,丙烯酸鏈狀烷基酯,丙烯酸環狀烷基酯,甲基丙烯酸芳基酯,丙烯酸芳基酯,不飽和二羧酸二酯,雙環不飽和化合物,馬來醯亞胺化合物,不飽和芳香族化合物,共軛二烯,具有四氫呋喃骨架、呋喃骨架、四氫吡喃骨架、吡喃骨架等的不飽和化合物及其他不飽和化合物等。 The compound (I-4) is not particularly limited as long as it is an unsaturated compound other than the compound (I-1), the compound (I-2) and the compound (I-3). Examples of the compound (I-4) include a chain alkyl methacrylate, a cyclic alkyl methacrylate, a chain alkyl acrylate, a cyclic alkyl acrylate, an aryl methacrylate, and an aryl acrylate. Base ester, unsaturated dicarboxylic acid diester, bicyclic unsaturated compound, maleic imine compound, unsaturated aromatic compound, conjugated diene, tetrahydrofuran skeleton, furan skeleton, tetrahydropyran skeleton, pyran skeleton Equal unsaturated compounds and other unsaturated compounds.
甲基丙烯酸鏈狀烷基酯例如可列舉甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸正丁酯、甲基丙烯酸仲丁酯、甲基丙烯酸第三丁酯、甲基丙烯酸-2-乙基己酯、甲基丙烯酸異癸酯、甲基丙烯酸正月桂基酯、甲基丙烯酸十三烷基酯、甲基丙烯酸正硬脂基酯等。 Examples of the chain alkyl methacrylate include methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, and methacrylic acid-2. Ethylhexyl ester, isodecyl methacrylate, n-lauryl methacrylate, tridecyl methacrylate, n-stearyl methacrylate, and the like.
甲基丙烯酸環狀烷基酯例如可列舉甲基丙烯酸環己 酯、甲基丙烯酸-2-甲基環己酯、甲基丙烯酸三環[5.2.1.02,6]癸烷-8-基酯、甲基丙烯酸三環[5.2.1.02,6]癸烷-8-基氧基乙酯、甲基丙烯酸異冰片酯等。 Examples of the cyclic alkyl methacrylate include cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, and tricyclo [5.2.1.0 2,6 ]decane-8-yl methacrylate. Tricyclo[meth] methacrylate [5.2.1.0 2,6 ]decane-8-yloxyethyl ester, isobornyl methacrylate, and the like.
丙烯酸鏈狀烷基酯例如可列舉丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丁酯、丙烯酸仲丁酯、丙烯酸第三丁酯、丙烯酸-2-乙基己酯、丙烯酸異癸酯、丙烯酸正月桂基酯、丙烯酸十三烷基酯、丙烯酸正硬脂基酯等。 Examples of the chain alkyl acrylate include methyl acrylate, ethyl acrylate, n-butyl acrylate, sec-butyl acrylate, tert-butyl acrylate, 2-ethylhexyl acrylate, isodecyl acrylate, and acrylic lauric acid. A base ester, a tridecyl acrylate, a n-stearyl acrylate or the like.
丙烯酸環狀烷基酯例如可列舉丙烯酸環己基酯、丙烯酸-2-甲基環己酯、丙烯酸三環[5.2.1.02,6]癸烷-8-基酯、丙烯酸三環[5.2.1.02,6]癸烷-8-基氧基乙酯、丙烯酸異冰片酯等。 Examples of the cyclic alkyl acrylate include cyclohexyl acrylate, 2-methylcyclohexyl acrylate, tricyclo[5.2.1.0 2,6 ]decane-8-yl acrylate, and tricyclohexyl acrylate [5.2.1.0]. 2,6 ]decane-8-yloxyethyl ester, isobornyl acrylate, and the like.
甲基丙烯酸芳基酯例如可列舉甲基丙烯酸苯基酯、甲基丙烯酸苄基酯等。 Examples of the aryl methacrylate include phenyl methacrylate and benzyl methacrylate.
丙烯酸芳基酯例如可列舉丙烯酸苯酯、丙烯酸苄酯等。 Examples of the aryl acrylate include phenyl acrylate and benzyl acrylate.
不飽和二羧酸二酯例如可列舉馬來酸二乙酯、富馬酸二乙酯、衣康酸二乙酯等。 Examples of the unsaturated dicarboxylic acid diester include diethyl maleate, diethyl fumarate, and diethyl itaconate.
雙環不飽和化合物例如可列舉雙環[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-甲氧基雙環[2.2.1]庚-2-烯、5-乙氧基雙環[2.2.1]庚-2-烯等。 Examples of the bicyclic unsaturated compound include bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene. 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, and the like.
馬來醯亞胺化合物例如可列舉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-(4-羥基苯基)馬來醯亞胺、N-(4-羥基苄基)馬來醯亞胺、N-琥珀醯亞胺基-3-馬來醯亞胺苯甲酸酯、N-琥珀醯亞胺基-4-馬來醯亞胺 丁酸酯、N-琥珀醯亞胺基-6-馬來醯亞胺己酸酯、N-琥珀醯亞胺基-3-馬來醯亞胺丙酸酯、N-(9-吖啶基)馬來醯亞胺等。 Examples of the maleic imine compound include N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, and N-(4-hydroxyphenyl)male. Yttrium, N-(4-hydroxybenzyl)maleimide, N-succinimide-3-maleimide benzoate, N-succinimide-4-ma Yttrium Butyrate, N-succinimide-6-maleimide caproate, N-succinimide-3-maleimide propionate, N-(9-acridinyl) ) Maleidin and the like.
不飽和芳香族化合物例如可列舉苯乙烯、α-甲基苯乙烯、間甲基苯乙烯、對甲基苯乙烯、乙烯基甲苯、對甲氧基苯乙烯等。 Examples of the unsaturated aromatic compound include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene.
共軛二烯例如可列舉1,3-丁二烯、異戊二烯、2,3-二甲基-1,3-丁二烯等。 Examples of the conjugated diene include 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene.
含有四氫呋喃骨架的不飽和化合物例如可列舉(甲基)丙烯酸四氫呋喃甲基酯、2-甲基丙烯醯氧基-丙酸四氫呋喃甲基酯、3-(甲基)丙烯醯氧基四氫呋喃-2-酮等。 Examples of the unsaturated compound containing a tetrahydrofuran skeleton include tetrahydrofuran methyl (meth)acrylate, 2-methylpropenyloxy-propionic acid tetrahydrofuran methyl ester, and 3-(methyl)acryloxytetrahydrofuran-2- Ketones, etc.
含有呋喃骨架的不飽和化合物例如可列舉2-甲基-5-(3-呋喃基)-1-戊烯-3-酮、(甲基)丙烯酸糠基酯、1-呋喃-2-丁基-3-烯-2-酮、1-呋喃-2-丁基-3-甲氧基-3-烯-2-酮、6-(2-呋喃基)-2-甲基-1-己烯-3-酮、6-呋喃-2-基-己-1-烯-3-酮、丙烯酸-2-呋喃-2-基-1-甲基-乙基酯、6-(2-呋喃基)-6-甲基-1-庚烯-3-酮等。 Examples of the unsaturated compound containing a furan skeleton include 2-methyl-5-(3-furyl)-1-penten-3-one, decyl (meth)acrylate, and 1-furan-2-butyl. 3-en-2-one, 1-furan-2-butyl-3-methoxy-3-en-2-one, 6-(2-furyl)-2-methyl-1-hexene 3-ketone, 6-furan-2-yl-hex-1-en-3-one, 2-furan-2-yl-1-methyl-ethyl acrylate, 6-(2-furanyl) -6-Methyl-1-hepten-3-one and the like.
含有四氫吡喃骨架的不飽和化合物例如可列舉甲基丙烯酸(四氫吡喃-2-基)甲酯、2,6-二甲基-8-(四氫吡喃-2-基氧基)-辛-1-烯-3-酮、2-甲基丙烯酸四氫吡喃-2-基酯、1-(四氫吡喃-2-氧基)-丁基-3-烯-2-酮等。 Examples of the unsaturated compound containing a tetrahydropyran skeleton include (tetrahydropyran-2-yl)methyl methacrylate and 2,6-dimethyl-8-(tetrahydropyran-2-yloxy). )-oct-1-en-3-one, 2-hydropyran-2-yl methacrylate, 1-(tetrahydropyran-2-yloxy)-butyl-3-ene-2- Ketones, etc.
含有吡喃骨架的不飽和化合物例如可列舉4-(1,4-二氧雜-5-氧代-6-庚烯基)-6-甲基-2-吡喃、4-(1,5-二氧雜-6-氧代-7-辛烯基)-6-甲基-2-吡喃等。 Examples of the unsaturated compound containing a pyran skeleton include 4-(1,4-dioxa-5-oxo-6-heptenyl)-6-methyl-2-pyran, 4-(1,5). -Dioxa-6-oxo-7-octenyl)-6-methyl-2-pyran and the like.
其他不飽和化合物例如可列舉丙烯腈、甲基丙烯腈、 氯乙烯、偏二氯乙烯、丙烯醯胺、甲基丙烯醯胺、乙酸乙烯酯等。 Examples of other unsaturated compounds include acrylonitrile and methacrylonitrile. Vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, and the like.
該些(I-4)化合物中,優選甲基丙烯酸鏈狀烷基酯、甲基丙烯酸環狀烷基酯、甲基丙烯酸芳基酯、馬來醯亞胺化合物、四氫呋喃骨架、呋喃骨架、四氫吡喃骨架、吡喃骨架、不飽和芳香族化合物、丙烯酸環狀烷基酯。自共聚反應性及對於鹼性水溶液的溶解性的方面考慮,該些化合物中更優選苯乙烯、甲基丙烯酸甲酯、甲基丙烯酸第三丁酯、甲基丙烯酸正月桂基酯、甲基丙烯酸苄基酯、甲基丙烯酸三環[5.2.1.02,6]癸烷-8-基酯、對甲氧基苯乙烯、丙烯酸-2-甲基環己酯、N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、(甲基)丙烯酸四氫呋喃甲基酯、聚乙二醇(n=2~10)單(甲基)丙烯酸酯、3-(甲基)丙烯醯氧基四氫呋喃-2-酮。該些(I-4)化合物可單獨使用亦可將2種以上混合使用。 Among these (I-4) compounds, a linear alkyl methacrylate, a cyclic alkyl methacrylate, an aryl methacrylate, a maleimide compound, a tetrahydrofuran skeleton, a furan skeleton, and four are preferable. Hydropyran skeleton, pyran skeleton, unsaturated aromatic compound, cyclic alkyl acrylate. Among these compounds, styrene, methyl methacrylate, butyl methacrylate, n-lauryl methacrylate, methacrylic acid are more preferable from the viewpoints of copolymerization reactivity and solubility in an aqueous alkaline solution. Benzyl ester, tricyclo [5.0.1.02 2,6 ]decane-8-yl methacrylate, p-methoxystyrene, 2-methylcyclohexyl acrylate, N-phenyl malayan Amine, N-cyclohexylmaleimide, tetrahydrofuranmethyl (meth)acrylate, polyethylene glycol (n=2~10) mono(meth)acrylate, 3-(methyl)propene oxide Tetrahydrofuran-2-one. These (I-4) compounds may be used singly or in combination of two or more.
作為(I-4)化合物的使用比例,基於(I-1)化合物、(I-2)化合物以及(I-4)化合物(及任意的(I-3)化合物)的合計而言,優選為10質量%~80質量%。 The ratio of use of the compound (I-4) is preferably based on the total of the (I-1) compound, the (I-2) compound, and the (I-4) compound (and any (I-3) compound). 10% by mass to 80% by mass.
[I]鹼溶性樹脂例如可通過在溶劑中,聚合起始劑的存在下,使上述(I-1)化合物以及(I-2)化合物(任意的(I-3)化合物及(I-4)化合物)共聚而製造。通過該合成方法,可合成至少包含含有環氧基的結構單元的共聚物。 [I] an alkali-soluble resin can be, for example, a compound of the above (I-1) and a compound of (I-2) (any compound of (I-3) and (I-4) in the presence of a polymerization initiator in a solvent. The compound) is produced by copolymerization. By this synthesis method, a copolymer containing at least a structural unit containing an epoxy group can be synthesized.
用以製造[I]鹼溶性樹脂的聚合反應中所使用的溶劑例如可列舉醇、二醇醚、乙二醇烷基醚乙酸酯、二乙二醇 單烷基醚、二乙二醇二烷基醚、二丙二醇二烷基醚、丙二醇單烷基醚、丙二醇烷基醚乙酸酯、丙二醇單烷基醚丙酸酯、酮、酯等。 The solvent used in the polymerization reaction for producing the [I] alkali-soluble resin may, for example, be an alcohol, a glycol ether, an ethylene glycol alkyl ether acetate, or a diethylene glycol. Monoalkyl ether, diethylene glycol dialkyl ether, dipropylene glycol dialkyl ether, propylene glycol monoalkyl ether, propylene glycol alkyl ether acetate, propylene glycol monoalkyl ether propionate, ketone, ester, and the like.
用以製造[I]鹼溶性樹脂的聚合反應中所使用的聚合起始劑通常可使用已知為自由基聚合起始劑的化合物。自由基聚合起始劑例如可列舉2,2'-偶氮雙異丁腈(AIBN)、2,2'-偶氮雙-(2,4-二甲基戊腈)、2,2'-偶氮雙-(4-甲氧基-2,4-二甲基戊腈)等偶氮化合物。 As the polymerization initiator used in the polymerization for producing the [I] alkali-soluble resin, a compound known as a radical polymerization initiator can be usually used. Examples of the radical polymerization initiator include 2,2'-azobisisobutyronitrile (AIBN), 2,2'-azobis-(2,4-dimethylvaleronitrile), 2,2'- An azo compound such as azobis-(4-methoxy-2,4-dimethylvaleronitrile).
在用以製造[I]鹼溶性樹脂的聚合反應中,為了調整分子量,可使用分子量調整劑。分子量調整劑例如可列舉氯仿、四溴化碳等鹵代烴類;正己硫醇、正辛硫醇、正十二烷硫醇、第三-十二烷硫醇、巰基乙酸等硫醇類;硫化二甲基黃原酸酯、二硫化二異丙基黃原酸酯等黃原酸酯類;異松油烯、α-甲基苯乙烯二聚物等。 In the polymerization reaction for producing the [I] alkali-soluble resin, a molecular weight modifier may be used in order to adjust the molecular weight. Examples of the molecular weight modifier include halogenated hydrocarbons such as chloroform and carbon tetrabromide; mercaptans such as n-hexyl mercaptan, n-octyl mercaptan, n-dodecyl mercaptan, tert-dodecyl mercaptan, and mercaptoacetic acid; Xanthogenates such as dimethyl xanthate sulfide and diisopropyl xanthate disulfide; tertylene olefin, α-methyl styrene dimer, and the like.
[I]鹼溶性樹脂的重量平均分子量(Mw)優選為1,000~30,000,更優選為5,000~20,000。通過使[I]鹼溶性樹脂的Mw為上述範圍,可使著色組成物的感光度及顯影性提高。另外,本說明書中的聚合物的Mw及數量平均分子量(Mn)可通過利用下述條件的凝膠滲透色譜法(GPC)而測定。 The weight average molecular weight (Mw) of the [I] alkali-soluble resin is preferably from 1,000 to 30,000, more preferably from 5,000 to 20,000. When the Mw of the [I] alkali-soluble resin is in the above range, the sensitivity and developability of the colored composition can be improved. Further, the Mw and the number average molecular weight (Mn) of the polymer in the present specification can be measured by gel permeation chromatography (GPC) using the following conditions.
裝置:GPC-101(昭和電工製造) Device: GPC-101 (made by Showa Denko)
管柱:將GPC-KF-801、GPC-KF-802、GPC-KF-803及GPC-KF-804加以結合 Column: Combine GPC-KF-801, GPC-KF-802, GPC-KF-803 and GPC-KF-804
流動相:四氫呋喃 Mobile phase: tetrahydrofuran
管柱溫度:40℃ Column temperature: 40 ° C
流速:1.0 mL/min Flow rate: 1.0 mL/min
試樣濃度:1.0質量% Sample concentration: 1.0% by mass
試樣注入量:100 μL Sample injection amount: 100 μL
檢測器:示差折射儀 Detector: differential refractometer
標準物質:單分散聚苯乙烯 Reference material: monodisperse polystyrene
而且,[I]鹼溶性樹脂例如可使能夠使用上述(I-1)化合物的1種以上而合成的共聚物(以下亦稱為“特定共聚物”)與上述(I-2)化合物進行反應而合成。利用該合成方法,可合成至少包含具有(甲基)丙烯醯氧基的結構單元的共聚物。 In addition, the [I] alkali-soluble resin can be reacted with the above-mentioned (I-2) compound by using a copolymer (hereinafter also referred to as "specific copolymer") which can be synthesized using one or more of the above compounds (I-1). And synthesis. By this synthesis method, a copolymer containing at least a structural unit having a (meth) acryloxy group can be synthesized.
[I]鹼溶性樹脂所含的具有(甲基)丙烯醯氧基的結構單元如下述式(3)所示。該結構單元是源自(I-1)化合物的特定共聚物中的羧基與(I-2)化合物的環氧基反應,形成酯鍵而獲得。 [I] The structural unit having a (meth) acryloxy group contained in the alkali-soluble resin is represented by the following formula (3). This structural unit is obtained by reacting a carboxyl group in a specific copolymer derived from the compound (I-1) with an epoxy group of the compound (I-2) to form an ester bond.
在上述式(3)中,R20及R21分別獨立為氫原子或甲 基。c為1~6的整數。R22是下述式(4-1)或式(4-2)所表示的2價基。 In the above formula (3), R 20 and R 21 each independently represent a hydrogen atom or a methyl group. c is an integer from 1 to 6. R 22 is a divalent group represented by the following formula (4-1) or formula (4-2).
在上述式(4-1)中,R23為氫原子或甲基。在上述式(4-1)及式(4-2)中,*表示與氧原子鍵結的部位。 In the above formula (4-1), R 23 is a hydrogen atom or a methyl group. In the above formula (4-1) and formula (4-2), * represents a site bonded to an oxygen atom.
關於上述式(3)所表示的結構單元,例如在使作為(I-2)化合物的甲基丙烯酸縮水甘油酯、甲基丙烯酸-2-甲基縮水甘油酯等化合物與具有羧基的共聚物反應的情況時,式(3)中的R22成為式(4-1)。另一方面,在使作為(I-2)化合物的甲基丙烯酸-3,4-環氧環己基甲酯等化合物與具有羧基的共聚物反應的情況時,式(3)中的R22成為式(4-2)。 With respect to the structural unit represented by the above formula (3), for example, a compound such as glycidyl methacrylate or 2-methylglycidyl methacrylate as a compound (I-2) is reacted with a copolymer having a carboxyl group. In the case, R 22 in the formula (3) becomes the formula (4-1). On the other hand, when a compound such as -3,4-epoxycyclohexylmethyl methacrylate as the compound (I-2) is reacted with a copolymer having a carboxyl group, R 22 in the formula (3) becomes Formula (4-2).
在合成特定共聚物時,亦可使用(I-1)化合物以外的化合物,例如上述(I-3)化合物、(I-4)化合物等作為共聚成分。自共聚反應性的方面考慮,該些化合物優選為甲基丙烯酸甲酯、甲基丙烯酸正丁酯、甲基丙烯酸苄酯、甲基丙烯酸-2-羥基乙酯、甲基丙烯酸三環[5.2.1.02,6]癸烷-8-基酯、苯乙烯、對甲氧基苯乙烯、甲基丙烯酸四氫呋喃-2-基酯、1,3-丁二烯。 In the synthesis of the specific copolymer, a compound other than the compound (I-1), for example, the above compound (I-3), the compound (I-4), or the like may be used as a copolymerization component. From the viewpoint of copolymerization reactivity, the compounds are preferably methyl methacrylate, n-butyl methacrylate, benzyl methacrylate, 2-hydroxyethyl methacrylate, trimethyl methacrylate [5.2. 1.0 2,6 ]decane-8-yl ester, styrene, p-methoxystyrene, tetrahydrofuran-2-yl methacrylate, 1,3-butadiene.
特定共聚物的共聚方法例如可列舉在溶劑中使用自由基聚合起始劑,使(I-1)化合物、及視需要的(I-3)化合物等進行聚合的方法。自由基聚合起始劑可列舉與上述[I]鹼溶性樹脂的項目中所例示的自由基聚合起始劑相同者。作為自由基聚合起始劑的使用量,相對於聚合性不飽和化合物100質量%而言,通常為0.1質量%~50質量%,優選為0.1質量%~20質量%。特定共聚物可於聚合反應溶液中直接供至[I]鹼溶性樹脂的製造中,也可以在將共聚物暫時自溶液中分離後,供至[I]鹼溶性樹脂的製造中。 The copolymerization method of the specific copolymer is, for example, a method in which a (I-1) compound and, if necessary, a compound (I-3) are polymerized, using a radical polymerization initiator in a solvent. The radical polymerization initiator is the same as the radical polymerization initiator exemplified in the item of the above [I] alkali-soluble resin. The amount of the radical polymerization initiator to be used is usually 0.1% by mass to 50% by mass, and preferably 0.1% by mass to 20% by mass based on 100% by mass of the polymerizable unsaturated compound. The specific copolymer may be directly supplied to the [I] alkali-soluble resin in the polymerization reaction solution, or may be supplied to the [I] alkali-soluble resin after the copolymer is temporarily separated from the solution.
特定共聚物的Mw優選為2,000~100,000,更優選為5,000~50,000。通過使Mw為2,000以上,可獲得著色組成物的充分的顯影寬容度,且可防止所形成的塗膜的殘膜率(圖案狀薄膜適當地殘存的比率)的降低,進一步良好地保持所得的圖案的形狀或耐熱性等。另一方面,通過使Mw為100,000以下,可保持高度的感光度,獲得良好的圖案形狀。而且,特定共聚物的分子量分佈(Mw/Mn)優選為5.0以下,更優選為3.0以下。通過使Mw/Mn為5.0以下,可良好地保持所得的間隔件圖案的形狀。而且,包含具有上述特定範圍的Mw/Mn的特定共聚物的著色組成物具有高度的顯影性,在顯影步驟中,可不產生顯影殘留地且容易地形成規定圖案形狀。 The Mw of the specific copolymer is preferably from 2,000 to 100,000, more preferably from 5,000 to 50,000. When Mw is 2,000 or more, sufficient development latitude of the colored composition can be obtained, and the residual film ratio of the formed coating film (ratio of the pattern film remaining properly) can be prevented from being lowered, and the obtained product can be further favorably maintained. The shape of the pattern or heat resistance. On the other hand, by setting Mw to 100,000 or less, a high degree of sensitivity can be maintained, and a good pattern shape can be obtained. Further, the molecular weight distribution (Mw/Mn) of the specific copolymer is preferably 5.0 or less, and more preferably 3.0 or less. By setting Mw/Mn to 5.0 or less, the shape of the obtained spacer pattern can be favorably maintained. Further, the coloring composition containing the specific copolymer having the above-specified range of Mw/Mn has high developability, and in the developing step, a predetermined pattern shape can be easily formed without causing development residue.
[I]鹼溶性樹脂的源自(I-1)化合物的結構單元的含有率優選為5質量%~60質量%,更優選為7質量%~50質量%,特別優選為8質量%~40質量%。 The content of the structural unit derived from the (I-1) compound of the [I] alkali-soluble resin is preferably 5% by mass to 60% by mass, more preferably 7% by mass to 50% by mass, and particularly preferably 8% by mass to 40% by mass. quality%.
[I]鹼溶性樹脂的源自(I-1)化合物以外的(I-3)化合物、(I-4)化合物等化合物的結構單元的含有率優選為10質量%~90質量%、更優選20質量%~80質量%。 The content of the structural unit of the compound (I-3) or the compound (I-4) other than the compound (I-1), which is an alkali-soluble resin, is preferably 10% by mass to 90% by mass, more preferably 20% by mass to 80% by mass.
在特定共聚物與(I-2)化合物的反應中,視需要在適當催化劑的存在下,優選在包含聚合抑制劑的共聚物溶液中,投入具有環氧基的不飽和化合物,在加溫下進行規定時間的攪拌。上述催化劑例如可列舉四丁基溴化銨等。上述聚合抑制劑例如可列舉對甲氧基苯酚等。反應溫度優選為70℃~100℃。反應時間優選為8小時~12小時。 In the reaction of the specific copolymer with the compound (I-2), if necessary, an unsaturated compound having an epoxy group is introduced in the presence of a suitable catalyst, preferably in a copolymer solution containing a polymerization inhibitor, under heating Stir for a specified period of time. Examples of the catalyst include tetrabutylammonium bromide and the like. Examples of the polymerization inhibitor include p-methoxyphenol and the like. The reaction temperature is preferably from 70 ° C to 100 ° C. The reaction time is preferably from 8 hours to 12 hours.
作為(I-2)化合物的使用比例,相對於共聚物中的源自(I-1)化合物的羧基而言,優選為5質量%~99質量%,更優選為10質量%~97質量%。通過使(I-2)化合物的使用比例為上述範圍,可使與共聚物的反應性、硬化膜的硬化性等進一步提高。(I-2)化合物可單獨使用或者將2種以上混合使用。 The use ratio of the compound (I-2) is preferably 5% by mass to 99% by mass, and more preferably 10% by mass to 97% by mass based on the carboxyl group derived from the (I-1) compound in the copolymer. . When the ratio of use of the compound (I-2) is in the above range, the reactivity with the copolymer, the curability of the cured film, and the like can be further improved. (I-2) The compounds may be used singly or in combination of two or more.
對本實施形態的彩色濾光片的製造中所使用的本實施形態的著色組成物中所含有的[II]聚合性化合物加以說明。 The [II] polymerizable compound contained in the coloring composition of the present embodiment used in the production of the color filter of the present embodiment will be described.
[II]聚合性化合物是具有乙烯性不飽和鍵的聚合性化合物。 [II] The polymerizable compound is a polymerizable compound having an ethylenically unsaturated bond.
可作為[II]聚合性化合物而使用的化合物例如可列舉:ω-羧基聚己內酯單(甲基)丙烯酸酯、乙二醇(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基) 丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、聚丙二醇二(甲基)丙烯酸酯、雙苯氧基乙醇茀二(甲基)丙烯酸酯、二羥甲基三環癸烷二(甲基)丙烯酸酯、甲基丙烯酸-2-羥基-3-(甲基)丙烯醯氧基丙基酯、(甲基)丙烯酸-2-(2'-乙烯氧基乙氧基)乙酯、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、磷酸三(2-(甲基)丙烯醯氧基乙基)酯、環氧乙烷改質二季戊四醇六丙烯酸酯、琥珀酸改質季戊四醇三丙烯酸酯等,除此以外還可以列舉具有直鏈伸烷基及脂環族結構且具有2個以上異氰酸酯基的化合物與在分子內具有1個以上羥基且具有3個~5個(甲基)丙烯醯氧基的化合物反應而所得的聚胺酯(甲基)丙烯酸酯化合物等。 Examples of the compound which can be used as the [II] polymerizable compound include ω -carboxypolycaprolactone mono(meth)acrylate, ethylene glycol (meth)acrylate, and 1,6-hexanediol II ( Methyl) acrylate, 1,9-nonanediol di(meth) acrylate, tetraethylene glycol di(meth) acrylate, polyethylene glycol di(meth) acrylate, polypropylene glycol di(a) Acrylate, bisphenoxyethanol hydrazine di(meth) acrylate, dimethylol tricyclodecane di(meth) acrylate, 2-hydroxy-3-(methyl) methacrylate醯oxypropyl ester, 2-(2'-vinyloxyethoxy)ethyl (meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate , pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tris(2-(methyl) propylene methoxyethyl) phosphate, epoxy Ethyl modified dipentaerythritol hexaacrylate, succinic acid modified pentaerythritol triacrylate, etc., and other examples thereof include a linear alkyl group and an alicyclic structure and having two or more isocyanides. An ester group with a compound having at least one hydroxyl group in the molecule and having three to five (meth) Bing Xixi group of polyurethane obtained by reacting (meth) acrylate compound.
可使用的[II]聚合性化合物的市售品例如可列舉:ARONIX(注冊商標)M-400、ARONIX M-402、ARONIX M-405、ARONIX M-450、ARONIX M-1310、ARONIX M-1600、ARONIX M-1960、ARONIX M-7100、ARONIX M-8030、ARONIX M-8060、ARONIX M-8100、ARONIX M-8530、ARONIX M-8560、ARONIX M-9050、ARONIX(注冊商標)TO-756、ARONIX TO-1450、ARONIX TO-1382(以上由東亞合成公司製造)、KAYARAD(注冊商標)DPHA、KAYARAD DPCA-20、KAYARAD DPCA-30、KAYARAD DPCA-60、KAYARAD DPCA-120、KAYARAD MAX-3510(以上由日本化藥公司製造)、 Viscoat 295、Viscoat 300、Viscoat 360、Viscoat GPT、Viscoat 3PA、Viscoat 400(以上由大阪有機化學工業公司製造)、作為聚胺酯丙烯酸酯類化合物的New frontier(注冊商標)R-1150(第一工業制藥公司)、KAYARAD(注冊商標)DPHA、KAYARAD(注冊商標)DPHA-40H、UX-5000(日本化藥公司)、UN-9000H(根上工業公司)、ARONIX(注冊商標)M-5300、ARONIX M-5600、ARONIX M-5700、ARONIX M-210、ARONIX M-220、ARONIX M-240、ARONIX M-270、ARONIX M-6200、ARONIX M-305、ARONIX M-309、ARONIX M-310、ARONIX M-315(以上由東亞合成公司製造)、KAYARAD(注冊商標)HDDA、KAYARAD(注冊商標)HX-220、KAYARAD HX-620、KAYARAD R-526、KAYARAD R-167、KAYARAD R-604、KAYARAD R-684、KAYARAD R-551、KAYARAD R-712、UX-2201、UX-2301、UX-3204、UX-3301、UX-4101、UX-6101、UX-7101、UX-8101、UX-0937、MU-2100、MU-4001(以上由日本化藥公司製造)、Artresin UN-9000PEP、Artresin UN-9200A、Artresin UN-7600、Artresin UN-333、Artresin UN-1003、Artresin UN-1255、Artresin UN-6060PTM、Artresin UN-6060P、Artresin SH-500B(以上由根上工業公司製造)、Viscoat 260、Viscoat 312、Viscoat 335HP(以上由大阪有機化學工業公司製造)等。 Commercial products of the [II] polymerizable compound which can be used include, for example, ARONIX (registered trademark) M-400, ARONIX M-402, ARONIX M-405, ARONIX M-450, ARONIX M-1310, ARONIX M-1600. , ARONIX M-1960, ARONIX M-7100, ARONIX M-8030, ARONIX M-8060, ARONIX M-8100, ARONIX M-8530, ARONIX M-8560, ARONIX M-9050, ARONIX (registered trademark) TO-756, ARONIX TO-1450, ARONIX TO-1382 (manufactured by Toagosei Co., Ltd.), KAYARAD (registered trademark) DPHA, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60, KAYARAD DPCA-120, KAYARAD MAX-3510 ( The above is manufactured by Nippon Kayaku Co., Ltd.) Viscoat 295, Viscoat 300, Viscoat 360, Viscoat GPT, Viscoat 3PA, Viscoat 400 (above manufactured by Osaka Organic Chemical Industry Co., Ltd.), New Frontier (registered trademark) R-1150 as a polyurethane acrylate compound (First Industrial Pharmaceutical Co., Ltd.) Company), KAYARAD (registered trademark) DPHA, KAYARAD (registered trademark) DPHA-40H, UX-5000 (Nippon Chemical Co., Ltd.), UN-9000H (Guanshang Industrial Co., Ltd.), ARONIX (registered trademark) M-5300, ARONIX M- 5600, ARONIX M-5700, ARONIX M-210, ARONIX M-220, ARONIX M-240, ARONIX M-270, ARONIX M-6200, ARONIX M-305, ARONIX M-309, ARONIX M-310, ARONIX M- 315 (above manufactured by Toagosei Co., Ltd.), KAYARAD (registered trademark) HDDA, KAYARAD (registered trademark) HX-220, KAYARAD HX-620, KAYARAD R-526, KAYARAD R-167, KAYARAD R-604, KAYARAD R-684 , KAYARAD R-551, KAYARAD R-712, UX-2201, UX-2301, UX-3204, UX-3301, UX-4101, UX-6101, UX-7101, UX-8101, UX-0937, MU-2100 , MU-4001 (above manufactured by Nippon Kayaku Co., Ltd.), Artresin UN-9000PEP, Artresin UN-9200A, Artresin UN-7600, Artresin UN-333, Artresin UN-1003 Artresin UN-1255, Artresin UN-6060PTM, Artresin UN-6060P, Artresin SH-500B (manufactured by the above root Industry Co.), Viscoat 260, Viscoat 312, Viscoat 335HP (manufactured by Osaka Organic Chemical Industry above, Inc.).
[II]聚合性化合物可單獨使用或者將2種以上混合使 用。作為著色組成物中的[II]聚合性化合物的使用比例,相對於[I]鹼溶性樹脂100質量份而言優選為10質量份~700質量份,更優選為20質量份~600質量份。通過使[II]聚合性化合物的使用比例為上述範圍,則著色組成物即使在低曝光量下亦可形成具有充分的耐熱性、耐溶劑性、電壓保持率的著色圖案等。 [II] The polymerizable compound may be used singly or in combination of two or more. use. The use ratio of the [II] polymerizable compound in the coloring composition is preferably 10 parts by mass to 700 parts by mass, and more preferably 20 parts by mass to 600 parts by mass, per 100 parts by mass of the [I] alkali-soluble resin. When the use ratio of the [II] polymerizable compound is in the above range, the colored composition can form a colored pattern having sufficient heat resistance, solvent resistance, and voltage holding ratio even at a low exposure amount.
對本實施形態的彩色濾光片的製造中所使用的本實施形態的著色組成物中所含有的[III]聚合起始劑加以說明。 The [III] polymerization initiator contained in the coloring composition of the present embodiment used in the production of the color filter of the present embodiment will be described.
[III]聚合起始劑是感放射線性聚合起始劑,是感應放射線而生成可引發[II]聚合性化合物的聚合的活性種的成分。此種[III]聚合起始劑可列舉O-醯基肟化合物、苯乙酮化合物、聯咪唑化合物等。該些化合物可單獨使用亦可將2種以上混合使用。 [III] The polymerization initiator is a radiation-sensitive polymerization initiator which is a component which induces radiation to form an active species which can initiate polymerization of the [II] polymerizable compound. Examples of such a [III] polymerization initiator include an O-indenyl hydrazine compound, an acetophenone compound, a biimidazole compound, and the like. These compounds may be used singly or in combination of two or more.
O-醯基肟化合物例如可列舉1,2-辛二酮-1-[4-(苯硫基)-2-(O-苯甲醯肟)]、乙酮-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-哢唑-3-基]-1-(O-乙醯肟)、1-[9-乙基-6-苯甲醯基-9H-哢唑-3-基]-辛烷-1-酮肟-O-乙酸酯、1-[9-乙基-6-(2-甲基苯甲醯基)-9H-哢唑-3-基]-乙烷-1-酮肟-O-苯甲酸酯、1-[9-正丁基-6-(2-乙基苯甲醯基)-9H-哢唑-3-基]-乙烷-1-酮肟-O-苯甲酸酯、乙酮-1-[9-乙基-6-(2-甲基-4-四氫呋喃基苯甲醯基)-9H-哢唑-3-基]-1-(O-乙醯肟)、乙酮-1-[9-乙基-6-(2-甲基-4-四氫吡喃基苯甲醯基)-9H-哢唑-3-基]-1-(O-乙醯 肟)、乙酮-1-[9-乙基-6-(2-甲基-5-四氫呋喃基苯甲醯基)-9H-哢唑-3-基]-1-(O-乙醯肟)、乙酮-1-[9-乙基-6-{2-甲基-4-(2,2-二甲基-1,3-二氧雜環戊烷基)甲氧基苯甲醯基}-9H-哢唑-3-基]-1-(O-乙醯肟)等。 Examples of the O-indenyl hydrazine compound include 1,2-octanedione-1-[4-(phenylthio)-2-(O-benzamide)], and ethyl ketone-1-[9-ethyl -6-(2-methylbenzimidyl)-9H-carbazol-3-yl]-1-(O-acetamidine), 1-[9-ethyl-6-benzylidene-9H -oxazol-3-yl]-octane-1-one oxime-O-acetate, 1-[9-ethyl-6-(2-methylbenzylidene)-9H-carbazole-3 -yl]-ethane-1-ketooxime-O-benzoate, 1-[9-n-butyl-6-(2-ethylbenzylidene)-9H-indazol-3-yl] -ethane-1-ketooxime-O-benzoate, ethyl ketone-1-[9-ethyl-6-(2-methyl-4-tetrahydrofuranylbenzylidene)-9H-carbazole- 3-yl]-1-(O-acetamidine), ethyl ketone-1-[9-ethyl-6-(2-methyl-4-tetrahydropyranylbenzylidene)-9H-oxime Zin-3-yl]-1-(O-acetonitrile 肟), Ethyl Ketone-1-[9-Ethyl-6-(2-methyl-5-tetrahydrofuranylbenzylidene)-9H-indazol-3-yl]-1-(O-acetamidine) Ethylketone-1-[9-ethyl-6-{2-methyl-4-(2,2-dimethyl-1,3-dioxolyl)methoxybenzimidazole }}-9H-carbazol-3-yl]-1-(O-acetamidine) and the like.
該些化合物中優選為1,2-辛二酮-1-[4-(苯硫基)-2-(O-苯甲醯肟)]、乙酮-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-哢唑-3-基]-1-(O-乙醯肟)、乙酮-1-[9-乙基-6-(2-甲基-4-四氫呋喃基甲氧基苯甲醯基)-9H-哢唑-3-基]-1-(O-乙醯肟)或乙酮-1-[9-乙基-6-{2-甲基-4-(2,2-二甲基-1,3-二氧雜環戊烷基)甲氧基苯甲醯基}-9H-哢唑-3-基]-1-(O-乙醯肟)。 Among these compounds, preferred is 1,2-octanedione-1-[4-(phenylthio)-2-(O-benzamide)], and ethyl ketone-1-[9-ethyl-6- (2-Methylbenzylidene)-9H-indazol-3-yl]-1-(O-acetamidine), ethyl ketone-1-[9-ethyl-6-(2-methyl- 4-tetrahydrofuranylmethoxybenzylidene)-9H-carbazol-3-yl]-1-(O-acetamidine) or ethyl ketone-1-[9-ethyl-6-{2- 4-(2,2-dimethyl-1,3-dioxolyl)methoxybenzylidene}-9H-indazol-3-yl]-1-(O-B醯肟).
苯乙酮化合物例如可列舉α-胺基酮化合物、α-羥基酮化合物。 Examples of the acetophenone compound include an α-amino ketone compound and an α-hydroxy ketone compound.
α-胺基酮化合物例如可列舉2-苄基-2-二甲基胺基-1-(4-嗎啉代苯基)-丁烷-1-酮、2-二甲基胺基-2-(4-甲基苄基)-1-(4-嗎啉-4-基-苯基)-丁烷-1-酮、2-甲基-1-(4-甲基噻吩基)-2-嗎啉代丙烷-1-酮等。 Examples of the α-amino ketone compound include 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one and 2-dimethylamino-2. -(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, 2-methyl-1-(4-methylthienyl)-2 - Morpholinopropan-1-one and the like.
α-羥基酮化合物例如可列舉1-苯基-2-羥基-2-甲基丙烷-1-酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙烷-1-酮、4-(2-羥基乙氧基)苯基-(2-羥基-2-丙基)酮、1-羥基環己基苯基酮等。 Examples of the α-hydroxyketone compound include 1-phenyl-2-hydroxy-2-methylpropan-1-one and 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1. a ketone, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone or the like.
該些化合物中優選α-胺基酮化合物,更優選2-苄基-2-二甲基胺基-1-(4-嗎啉代苯基)-丁烷-1-酮、2-二甲基胺基-2-(4-甲基苄基)-1-(4-嗎啉-4-基-苯基)-丁烷-1-酮、2-甲基-1-(4-甲基噻吩基)-2-嗎啉代丙烷-1-酮。 Among these compounds, an α-amino ketone compound is preferred, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, 2-dimethyl dimethyl ester is more preferred. Amino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, 2-methyl-1-(4-methyl Thienyl)-2-morpholinopropan-1-one.
聯咪唑化合物例如優選2,2'-雙(2-氯苯基)-4,4',5,5'-四苯基-1,2'-聯咪唑、2,2'-雙(2,4-二氯苯基)-4,4',5,5'-四苯基-1,2'-聯咪唑或2,2'-雙(2,4,6-三氯苯基)-4,4',5,5'-四苯基-1,2'-聯咪唑,其中更優選2,2'-雙(2,4-二氯苯基)-4,4',5,5'-四苯基-1,2'-聯咪唑。 The biimidazole compound is, for example, preferably 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2, 4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole or 2,2'-bis(2,4,6-trichlorophenyl)-4 , 4',5,5'-tetraphenyl-1,2'-biimidazole, of which 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5' is more preferred. -Tetraphenyl-1,2'-biimidazole.
作為[III]聚合起始劑的使用比例,相對於[I]鹼溶性樹脂100質量份而言,優選為1質量份~40質量份,更優選為5質量份~30質量份。通過使[III]聚合起始劑的使用比例為1質量份~40質量份,著色組成物即使於低曝光量的情況下亦可形成具有高的耐溶劑性等的著色圖案及彩色濾光片。 The use ratio of the [III] polymerization initiator is preferably from 1 part by mass to 40 parts by mass, more preferably from 5 parts by mass to 30 parts by mass, per 100 parts by mass of the [I] alkali-soluble resin. When the use ratio of the [III] polymerization initiator is from 1 part by mass to 40 parts by mass, the colored composition can form a color pattern and a color filter having high solvent resistance and the like even at a low exposure amount. .
如上所述,對著色圖案及具有該著色圖案的彩色濾光片強烈要求高的色純度、亮度、對比度等。因此,作為本實施形態的彩色濾光片的製造中所使用的本實施形態的著色組成物中所含有的[IV]著色劑,變得必需選擇適於實現此種特性的著色劑。[IV]著色劑例如可使用顏料、染料及天然色素的任意種。而且,於考慮對著色圖案及彩色濾光片所要求的高的色純度或亮度等的情況下,優選選擇顏料及染料,其中特別優選選擇染料。 As described above, high color purity, brightness, contrast, and the like are strongly required for the colored pattern and the color filter having the colored pattern. Therefore, as the [IV] coloring agent contained in the coloring composition of the present embodiment used in the production of the color filter of the present embodiment, it is necessary to select a coloring agent suitable for realizing such characteristics. As the colorant, for example, any of a pigment, a dye, and a natural pigment can be used. Further, in consideration of high color purity, brightness, and the like required for the colored pattern and the color filter, it is preferred to select a pigment and a dye, and among them, a dye is particularly preferably selected.
關於可作為[IV]著色劑而使用的染料,例如可列舉油溶性染料、酸性染料或其衍生物、直接染料、媒介染料等。作為染料,只要可溶於有機溶劑中,則可使用公知的染料。 Examples of the dye which can be used as the [IV] coloring agent include oil-soluble dyes, acid dyes or derivatives thereof, direct dyes, and vehicle dyes. As the dye, a known dye can be used as long as it is soluble in an organic solvent.
C.I.油溶性染料例如可列舉: C.I.溶劑黃4(以下省略“C.I.溶劑黃”的記載而僅僅記載編號。其他染料也同樣地進行記載)、14、15、23、24、38、62、63、68、82、88、94、98、99、162、179;C.I.溶劑紅45、49、125、130;C.I.溶劑橙2、7、11、15、26、56;C.I.溶劑藍35、37、59、67;C.I.溶劑綠1、3、4、5、7、28、29、32、33、34、35等。 C.I. Oil-soluble dyes, for example, CI Solvent Yellow 4 (hereinafter, the description of "CI Solvent Yellow" is omitted, and only the number is described. Other dyes are also described in the same manner), 14, 15, 23, 24, 38, 62, 63, 68, 82, 88, 94, 98, 99, 162, 179; CI solvent red 45, 49, 125, 130; CI solvent orange 2, 7, 11, 15, 26, 56; CI solvent blue 35, 37, 59, 67; CI solvent green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc.
C.I.酸性染料例如可列舉:C.I.酸性黃1、3、7、9、11、17、23、25、29、34、36、38、40、42、54、65、72、73、76、79、98、99、111、112、113、114、116、119、123、128、134、135、138、139、140、144、150、155、157、160、161、163、168、169、172、177、178、179、184、190、193、196、197、199、202、203、204、205、207、212、214、220、221、228、230、232、235、238、240、242、243、251;Valifast yellow 1101、1109、1151、3108、3120、3130、3150、3170、4120;C.I.酸性紅1、4、8、14、17、18、26、27、29、31、34、35、37、42、44、50、51、52、57、66、73、80、87、88、91、92、94、97、103、111、114、129、133、134、138、143、145、150、151、158、176、182、183、198、206、211、215、216、217、227、228、249、252、257、258、260、261、266、268、270、274、277、280、281、 195、308、312、315、316、339、341、345、346、349、382、383、394、401、412、417、418、422、426;C.I.酸性橙6、7、8、10、12、26、50、51、52、56、62、63、64、74、75、94、95、107、108、169、173;C.I.酸性藍1、7、9、15、18、23、25、27、29、40、42、45、51、62、70、74、80、83、86、87、90、92、96、103、108、112、113、120、129、138、147、150、158、171、182、192、210、242、249、243、256、259、267、278、280、285、290、296、315、324、335、340;C.I.酸性紫6B、7、9、17、19、49;C.I.酸性綠1、3、5、9、16、25、27、50、58、63、65、80、104、105、106、109;C.I.酸性黑24等染料。 Examples of the CI acid dyes include: CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; Valifast yellow 1101, 1109, 1151, 3108, 3120, 3130, 3150, 3170, 4120; CI acid red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35 , 37, 42, 44, 50, 51, 52, 57, 66, 73, 80, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145 , 150, 151, 158, 176, 182, 183, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277 280, 281, 195, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12 , 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; CI Acid Blue 1, 7, 9, 15, 18, 23, 25, 27, 29, 40, 42, 45, 51, 62, 70, 74, 80, 83, 86, 87, 90, 92, 96, 103, 108, 112, 113, 120, 129, 138, 147, 150, 158, 171, 182, 192, 210, 242, 249, 243, 256, 259, 267, 278, 280, 285, 290, 296, 315, 324, 335, 340; CI Acid Violet 6B, 7, 9, 17 19, 49; CI acid green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106, 109; CI acid black 24 and other dyes.
C.I.直接染料例如可列舉:C.I.直接黃2、33、34、35、38、39、43、47、50、54、58、68、69、70、71、86、93、94、95、98、102、108、109、129、136、138、141;C.I.直接紅79、82、83、84、91、92、96、97、98、99、105、106、107、172、173、176、177、179、181、182、184、204、207、211、213、218、220、221、222、232、233、234、241、243、246、250;C.I.直接橙34、39、41、46、50、52、56、57、61、64、65、68、70、96、97、106、107;C.I.直接藍57、77、80、81、84、85、86、90、93、 94、95、97、98、99、100、101、106、107、108、109、113、114、115、117、119、137、149、150、153、155、156、158、159、160、161、162、163、164、166、167、170、171、172、173、188、189、190、192、193、194、196、198、199、200、207、209、210、212、213、214、222、228、229、237、238、242、243、244、245、247、248、250、251、252、256、257、259、260、268、274、275、293;C.I.直接紫47、52、54、59、60、65、66、79、80、81、82、84、89、90、93、95、96、103、104;C.I.直接綠25、27、31、32、34、37、63、65、66、67、68、69、72、77、79、82等。 Examples of CI direct dyes include: CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177 ,179,181,182,184,204,207,211,213,218,220,221,222,232,233,234,241,243,246,250; CI Direct Orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI direct blue 57, 77, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 166, 167, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 196, 198, 199, 200, 207, 209, 210, 212, 213, 214, 222, 228, 229, 237, 238, 242, 243, 244, 245, 247, 248, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct Violet 47 , 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, and the like.
C.I.媒介染料例如可列舉:C.I.媒介黃5、8、10、16、20、26、30、31、33、42、43、45、56、61、62、65;C.I.媒介紅1、2、3、4、9、11、12、14、17、18、19、22、23、24、25、26、30、32、33、36、37、38、39、41、43、45、46、48、53、56、63、71、74、85、86、88、90、94、95;C.I.媒介橙3、4、5、8、12、13、14、20、21、23、24、28、29、32、34、35、36、37、42、43、47、48;C.I.媒介藍1、2、3、7、8、9、12、13、15、16、19、20、21、22、23、24、26、30、31、32、39、40、41、43、44、48、49、53、61、74、77、83、84; C.I.媒介紫1、2、4、5、7、14、22、24、30、31、32、37、40、41、44、45、47、48、53、58;C.I.媒介綠1、3、4、5、10、15、19、26、29、33、34、35、41、43、53等。 For CI medium dyes, for example, CI medium yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI medium red 1, 2, 3 , 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 30, 32, 33, 36, 37, 38, 39, 41, 43, 45, 46, 48 , 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95; CI medium orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI medium blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22 , 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI medium purple 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58; CI medium green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43, 53 and so on.
關於可作為[IV]著色劑而使用的顏料,可使用有機顏料、無機顏料的任意種。有機顏料例如可列舉在染料索引(C.I.;染色家協會(The Society of Dyers and Colourists)發行)中分類為顏料的化合物。具體而言可列舉附有如下所述的染料索引(C.I.)名的顏料。 As the pigment which can be used as the [IV] coloring agent, any of an organic pigment and an inorganic pigment can be used. The organic pigment may, for example, be a compound classified as a pigment in a dye index (C.I.; issued by The Society of Dyers and Colourists). Specifically, a pigment having a dye index (C.I.) name as described below can be cited.
可列舉:C.I.顏料黃12、C.I.顏料黃13、C.I.顏料黃14、C.I.顏料黃17、C.I.顏料黃20、C.I.顏料黃24、C.I.顏料黃31、C.I.顏料黃55、C.I.顏料黃83、C.I.顏料黃93、C.I.顏料黃109、C.I.顏料黃110、C.I.顏料黃138、C.I.顏料黃139、C.I.顏料黃150、C.I.顏料黃153、C.I.顏料黃154、C.I.顏料黃155、C.I.顏料黃166、C.I.顏料黃168、C.I.顏料黃180、C.I.顏料黃185、C.I.顏料黃211;C.I.顏料橙5、C.I.顏料橙13、C.I.顏料橙14、C.I.顏料橙24、C.I.顏料橙34、C.I.顏料橙36、C.I.顏料橙38、C.I.顏料橙40、C.I.顏料橙43、C.I.顏料橙46、C.I.顏料橙49、C.I.顏料橙61、C.I.顏料橙64、C.I.顏料橙68、C.I.顏料橙70、C.I.顏料橙71、C.I.顏料橙72、C.I.顏料橙73、C.I.顏料橙74;C.I.顏料紅1、C.I.顏料紅2、C.I.顏料紅5、C.I.顏料紅17、C.I.顏料紅31、C.I.顏料紅32、C.I.顏料紅41、C.I.顏 料紅122、C.I.顏料紅123、C.I.顏料紅144、C.I.顏料紅149、C.I.顏料紅166、C.I.顏料紅168、C.I.顏料紅170、C.I.顏料紅171、C.I.顏料紅175、C.I.顏料紅176、C.I.顏料紅177、C.I.顏料紅178、C.I.顏料紅179、C.I.顏料紅180、C.I.顏料紅185、C.I.顏料紅187、C.I.顏料紅202、C.I.顏料紅206、C.I.顏料紅207、C.I.顏料紅209、C.I.顏料紅214、C.I.顏料紅220、C.I.顏料紅221、C.I.顏料紅224、C.I.顏料紅242、C.I.顏料紅243、C.I.顏料紅254、C.I.顏料紅255、C.I.顏料紅262、C.I.顏料紅264、C.I.顏料紅272;C.I.顏料紫1、C.I.顏料紫19、C.I.顏料紫23、C.I.顏料紫29、C.I.顏料紫32、C.I.顏料紫36、C.I.顏料紫38;C.I.顏料藍15、C.I.顏料藍15:3、C.I.顏料藍15:4、C.I.顏料藍15:6、C.I.顏料藍60、C.I.顏料藍80;C.I.顏料綠7、C.I.顏料綠36、C.I.顏料綠58;C.I.顏料棕23、C.I.顏料棕25;C.I.顏料黑1、C.I.顏料黑7等。 Can be cited as: CI Pigment Yellow 12, CI Pigment Yellow 13, CI Pigment Yellow 14, CI Pigment Yellow 17, CI Pigment Yellow 20, CI Pigment Yellow 24, CI Pigment Yellow 31, CI Pigment Yellow 55, CI Pigment Yellow 83, CI Pigment Yellow 93, CI Pigment Yellow 109, CI Pigment Yellow 110, CI Pigment Yellow 138, CI Pigment Yellow 139, CI Pigment Yellow 150, CI Pigment Yellow 153, CI Pigment Yellow 154, CI Pigment Yellow 155, CI Pigment Yellow 166, CI Pigment Yellow 168, CI Pigment Yellow 180, CI Pigment Yellow 185, CI Pigment Yellow 211; CI Pigment Orange 5, CI Pigment Orange 13, CI Pigment Orange 14, CI Pigment Orange 24, CI Pigment Orange 34, CI Pigment Orange 36, CI Pigment Orange 38, CI Pigment Orange 40, CI Pigment Orange 43, CI Pigment Orange 46, CI Pigment Orange 49, CI Pigment Orange 61, CI Pigment Orange 64, CI Pigment Orange 68, CI Pigment Orange 70, CI Pigment Orange 71, CI Pigment Orange 72, CI Pigment Orange 73, CI Pigment Orange 74; CI Pigment Red 1, CI Pigment Red 2, CI Pigment Red 5, CI Pigment Red 17, CI Pigment Red 31, CI Pigment Red 32, CI Pigment Red 41, CI Yan Red 122, CI Pigment Red 123, CI Pigment Red 144, CI Pigment Red 149, CI Pigment Red 166, CI Pigment Red 168, CI Pigment Red 170, CI Pigment Red 171, CI Pigment Red 175, CI Pigment Red 176, CI Pigment Red 177, CI Pigment Red 178, CI Pigment Red 179, CI Pigment Red 180, CI Pigment Red 185, CI Pigment Red 187, CI Pigment Red 202, CI Pigment Red 206, CI Pigment Red 207, CI Pigment Red 209, CI Pigment Red 214, CI Pigment Red 220, CI Pigment Red 221, CI Pigment Red 224, CI Pigment Red 242, CI Pigment Red 243, CI Pigment Red 254, CI Pigment Red 255, CI Pigment Red 262, CI Pigment Red 264, CI Pigment red 272; CI pigment violet 1, CI pigment violet 19, CI pigment violet 23, CI pigment violet 29, CI pigment violet 32, CI pigment violet 36, CI pigment violet 38; CI pigment blue 15, CI pigment blue 15:3 , CI Pigment Blue 15:4, CI Pigment Blue 15:6, CI Pigment Blue 60, CI Pigment Blue 80; CI Pigment Green 7, CI Pigment Green 36, CI Pigment Green 58; CI Pigment Brown 23, CI Pigment Brown 25; CI Pigment Black 1, CI Pigment Black 7, etc.
其次,對作為染料或顏料等的[IV]著色劑的化學結構加以說明。關於化學結構,可列舉偶氮類、三芳基甲烷類、蒽醌類、苯亞甲基類、氧雜菁類、花菁類、吩噻嗪類、吡咯並吡唑偶氮甲鹼類、氧雜蒽類、酞菁類、苯並吡喃類、靛藍類、二酮基吡咯並吡咯類等。該些著色劑中優選選擇三芳基甲烷類、巴比妥酸偶氮類、吡唑偶氮類、苯胺基偶氮類、吡唑並三唑偶氮類、吡啶酮偶氮類、酞菁類、蒽醌類、蒽吡啶酮類及二酮基吡咯並吡咯類的著色劑。 Next, the chemical structure of the [IV] colorant as a dye or a pigment will be described. Examples of the chemical structure include azo, triarylmethane, anthracene, benzylidene, oxaphthalocyanine, cyanine, phenothiazine, pyrrolopyrazole azomethine, and oxygen. Heteroquinones, phthalocyanines, benzopyrans, indigo, diketopyrrolopyrroles, and the like. Among these colorants, triarylmethane, barbituric azo, pyrazole azo, anilino azo, pyrazolotriazole azo, pyridone azo, phthalocyanine are preferably selected. A coloring agent for quinones, anthraquinones and diketopyrrolopyrroles.
作為優選的[IV]著色劑的例子的三芳基甲烷類著色劑是呈藍色、紫色的著色劑。 A triarylmethane-based colorant which is an example of a preferred [IV] colorant is a blue, violet color former.
呈藍色、紫色的著色劑是屬於C.I.顏料藍、C.I.顏料紫等顏料,C.I.鹼性藍、C.I.鹼性紫等鹼性染料,C.I.溶劑藍、C.I.溶劑紫等油溶性染料、C.I.酸性藍、C.I.酸性紫等酸性染料,C.I.分散藍、C.I.分散紫等分散性染料等,C.I.食用藍、C.I.食用紫等食用著色劑等著色劑。 Blue and purple coloring agents are pigments such as CI Pigment Blue, CI Pigment Violet, CI Basic Blue, CI Basic Violet and other basic dyes, CI Solvent Blue, CI Solvent Violet and other oil-soluble dyes, CI Acid Blue, Acid dyes such as CI acid purple, disperse dyes such as CI disperse blue and CI disperse violet, and colorants such as CI food blue, CI edible violet, and other food coloring agents.
另外,屬於用反離子對該些酸性染料(亦包括直接染料)、鹼性染料進行改質而成的成鹽染料。 In addition, it is a salt-forming dye which is modified by using a counter ion to modify some of the acid dyes (including direct dyes) and basic dyes.
作為三芳基甲烷類著色劑的例子的三苯基甲烷類著色劑是由於位於相對於中心碳而言為對位的位置的NH2或OH基被氧化而成為醌結構,從而進行顯色的著色劑。而且,主要為鹼性染料,但導入了磺酸基的染料成為酸性染料。 The triphenylmethane-based colorant which is an example of a triarylmethane-based coloring agent is a color-developing coloring because the NH 2 or OH group located at a position opposite to the center carbon is oxidized to form a fluorene structure. Agent. Further, it is mainly a basic dye, but a dye into which a sulfonic acid group is introduced becomes an acid dye.
根據NH2、OH基的個數而分為以下3種類型,其中三胺基三苯基甲烷類染料的形態於顯示出良好的藍色方面而言為優選的形態。 The following three types are classified according to the number of NH 2 and OH groups, and the form of the triaminotriphenylmethane dye is a preferable form in terms of exhibiting a good blue color.
a)二胺基三苯基甲烷類染料 a) Diaminotriphenylmethane dyes
b)三胺基三苯基甲烷類染料 b) Triaminotriphenylmethane dyes
c)具有OH基的玫紅酸類染料 c) Rose sulphur dyes with OH groups
三胺基三苯基甲烷類染料的色調鮮明,耐光性優異而優選使用。而且,其中特別優選作為鹼性染料的二苯基萘基甲烷染料。 The triaminotriphenylmethane dye is preferably used because it has a clear color tone and is excellent in light resistance. Further, among them, a diphenylnaphthylmethane dye which is a basic dye is particularly preferable.
三芳基甲烷類著色劑可使用以下5種形態的染料及顏 料。 Triaryl methane colorants can use the following five forms of dyes and pigments material.
1)三芳基甲烷類染料的鹼性染料(三芳基甲烷類鹼性染料) 1) Basic dyes of triaryl methane dyes (triarylmethane basic dyes)
2)三芳基甲烷類鹼性染料與有機磺酸的成鹽化合物、三芳基甲烷類鹼性染料與芳香族羥基羧酸的成鹽化合物 2) salt-forming compounds of triarylmethane-based basic dyes and organic sulfonic acids, salt-forming compounds of triarylmethane-based basic dyes and aromatic hydroxycarboxylic acids
3)三芳基甲烷類染料的酸性染料 3) Acid dyes of triaryl methane dyes
4)三芳基甲烷類酸性染料與季銨的成鹽化合物 4) Salt formation compounds of triarylmethane acid dyes and quaternary ammonium
5)三芳基甲烷類染料的色澱顏料(特別是三芳基甲烷類染料的金屬色澱顏料) 5) Lake pigments of triarylmethane dyes (especially metal lake pigments of triarylmethane dyes)
作為該些形態,其中優選使用三芳基甲烷類染料的鹼性染料、三芳基甲烷類鹼性染料與有機磺酸的成鹽化合物、三芳基甲烷類鹼性染料與芳香族羥基羧酸的成鹽化合物、三芳基甲烷類染料的金屬色澱顏料。 As such a form, a basic dye using a triarylmethane dye, a salt forming compound of a triarylmethane-based basic dye and an organic sulfonic acid, a salt of a triarylmethane-based basic dye and an aromatic hydroxycarboxylic acid are preferably used. A metal lake pigment of a compound, a triarylmethane dye.
三芳基甲烷類染料具有如下的分光特性:在400 nm~430 nm中具有高的透射率。然而,即使具有良好的分光特性,也與一般的染料同樣地耐熱性極差。在要求高的可靠性的彩色液晶顯示元件中使用時,於先前,特性並不充分。因此,優選在可於低溫下製造的本實施形態的彩色濾光片中使用。而且,還可以像先前改善三芳基甲烷類染料的問題點那樣對染料進行鹼化、成鹽化、油溶性化、利用樹脂的改質而使用。或者還可以將染料色澱化而製成顏料。 The triarylmethane dye has the following spectral characteristics: high transmittance in the range of 400 nm to 430 nm. However, even if it has a good spectral characteristic, it is extremely inferior in heat resistance like a general dye. When used in a color liquid crystal display element requiring high reliability, the characteristics are not sufficient in the past. Therefore, it is preferably used in a color filter of the present embodiment which can be produced at a low temperature. Further, the dye may be alkalized, salified, oil-soluble, or modified with a resin as in the prior problem of improving the triarylmethane dye. Alternatively, the dye can be laked to form a pigment.
三芳基甲烷類染料的鹼性染料、油溶性染料優選通過與具有如羧基這樣的酸基的樹脂或松香酯、松香改質馬來 酸樹脂(松香改質富馬酸樹脂亦同義)混合而改善耐受性。該些具有酸基的樹脂、松香酯、松香改質馬來酸樹脂的酸值優選為20~200。此處,酸值是利用JIS K-0070的方法而測定的值。 The basic dye and the oil-soluble dye of the triarylmethane dye are preferably modified by a resin or a rosin ester having an acid group such as a carboxyl group, and a rosin-modified horse. The acid resin (rosin-modified fumarate resin is also synonymous) is mixed to improve the tolerance. The acid value of the resin having an acid group, the rosin ester, and the rosin-modified maleic acid resin is preferably 20 to 200. Here, the acid value is a value measured by the method of JIS K-0070.
三芳基甲烷類鹼性染料可列舉C.I.鹼性藍1、5、7、26、C.I.鹼性紫1、3等。其中優選使用C.I.鹼性藍7。 Examples of the triarylmethane-based basic dyes include C.I. Basic Blue 1, 5, 7, 26, C.I. Basic Violet 1, 3, and the like. Among them, C.I. Basic Blue 7 is preferably used.
其次,對三芳基甲烷類鹼性染料與有機磺酸的成鹽化合物加以說明。三芳基甲烷類鹼性染料與有機磺酸可通過使兩者溶解於水溶液、醇溶液中等,從而進行反應而獲得成鹽化合物。 Next, a salt-forming compound of a triarylmethane-based basic dye and an organic sulfonic acid will be described. The triarylmethane-based basic dye and the organic sulfonic acid can be reacted to obtain a salt-forming compound by dissolving both in an aqueous solution or an alcohol solution.
有機磺酸可使用萘類磺化物、萘酚類磺化物等。 As the organic sulfonic acid, a naphthalene sulfonate or a naphthol sulfonate can be used.
萘類磺化物是在萘的碳原子上鍵結有磺酸基的化合物的總稱,萘酚類磺化物是在萘酚的碳原子上鍵結有磺酸基的化合物的總稱。 The naphthalene sulfonate is a general term for a compound having a sulfonic acid group bonded to a carbon atom of naphthalene, and the naphthol sulfonate is a general term for a compound having a sulfonic acid group bonded to a carbon atom of naphthol.
萘類磺化物中存在有:鍵結有1個磺酸基的萘單磺酸、鍵結有2個磺酸基的萘二磺酸、鍵結有3個磺酸基的萘三磺酸。具體而言為1-萘磺酸、2-萘磺酸、1,3-萘二磺酸、1,5-萘二磺酸、1,6-萘二磺酸、1,7-萘二磺酸、2,6-萘二磺酸、2,7-萘二磺酸、1,3,5-萘三磺酸、1,3,6-萘三磺酸、1,3,7-萘三磺酸等。 Among the naphthalene sulfonates, there are naphthalene monosulfonic acid having one sulfonic acid group bonded thereto, naphthalene disulfonic acid having two sulfonic acid groups bonded thereto, and naphthalene trisulfonic acid having three sulfonic acid groups bonded thereto. Specifically, it is 1-naphthalenesulfonic acid, 2-naphthalenesulfonic acid, 1,3-naphthalenedisulfonic acid, 1,5-naphthalene disulfonic acid, 1,6-naphthalenedisulfonic acid, 1,7-naphthalene disulfide Acid, 2,6-naphthalenedisulfonic acid, 2,7-naphthalenedisulfonic acid, 1,3,5-naphthalenetrisulfonic acid, 1,3,6-naphthalenetrisulfonic acid, 1,3,7-naphthalene Sulfonic acid, etc.
而且,萘類磺化物除了上述萘磺酸以外亦包含萘胺磺酸。而且存在有:鍵結有1個磺酸基的萘胺單磺酸、鍵結有2個磺酸基的萘胺二磺酸、鍵結有3個磺酸基的萘胺三磺酸。具體而言為1,4-萘胺磺酸(對胺基萘磺酸)、1,5- 萘胺磺酸(勞倫酸)、1,6-萘胺磺酸(6-克利弗酸)、1,7-萘胺磺酸(7-克利弗酸)、1,8-萘胺磺酸(周位酸)、2,1-萘胺磺酸(托拜厄斯酸)、2,5-萘胺磺酸、2,6-萘胺磺酸(布龍酸)、1,3,6-萘胺二磺酸(弗羅因德酸)、1,3,7-萘胺二磺酸、2,3,6-萘胺二磺酸(胺基R酸)、2,4,6-萘胺二磺酸(C酸)、2,5,7-萘胺二磺酸(胺基J酸)、2,6,8-萘胺二磺酸(胺基G酸)、1,3,6,8-萘胺三磺酸(科赫酸)等。 Further, the naphthalene sulfonate contains naphthylamine sulfonic acid in addition to the above naphthalenesulfonic acid. Further, there are naphthylamine monosulfonic acid having one sulfonic acid group bonded thereto, naphthylamine disulfonic acid having two sulfonic acid groups bonded thereto, and naphthylamine trisulfonic acid having three sulfonic acid groups bonded thereto. Specifically, 1,4-naphthylaminesulfonic acid (p-aminonaphthalenesulfonic acid), 1,5- Naphthylamine sulfonic acid (lauranic acid), 1,6-naphthylamine sulfonic acid (6-cliphoric acid), 1,7-naphthylamine sulfonic acid (7-cliphoric acid), 1,8-naphthylamine sulfonic acid (peripheral acid), 2,1-naphthylamine sulfonic acid (Tobias acid), 2,5-naphthylamine sulfonic acid, 2,6-naphthylamine sulfonic acid (bromonic acid), 1,3,6 -naphthylamine disulfonic acid (Froud acid), 1,3,7-naphthylamine disulfonic acid, 2,3,6-naphthylamine disulfonic acid (amino R acid), 2,4,6- Naphthylamine disulfonic acid (C acid), 2,5,7-naphthylamine disulfonic acid (amino J acid), 2,6,8-naphthylamine disulfonic acid (amino G acid), 1,3, 6,8-naphthylamine trisulfonic acid (kohic acid) and the like.
萘酚類磺化物中亦存在有:鍵結有1個磺酸基的萘酚單磺酸、鍵結有2個磺酸基的萘酚二磺酸、鍵結有3個磺酸基的萘酚三磺酸。具體而言為1-萘酚-2-磺酸、1-萘酚-4-磺酸(NW酸)、1-萘酚-5-磺酸(L酸)、1-萘酚-8-磺酸、2-萘酚-1-磺酸、2-萘酚-6-磺酸(薛佛氏酸)、2-萘酚-8-磺酸(藏紅花酸)、1-萘酚-2,4-二磺酸、1-萘酚-3,6-二磺酸、1-萘酚-3,8-二磺酸(ε酸)、2-萘酚-3,6-二磺酸(R酸)、2-萘酚-3,8-二磺酸、2-萘酚-6,8-二磺酸(G酸)、1-萘酚-2,4,7-三磺酸、1-萘酚-3,6,8-三磺酸(氧代科赫酸)、2-萘酚-3,6,8-三磺酸等。 Among the naphthol sulfonates, there are also naphthol monosulfonic acid bonded with one sulfonic acid group, naphthol disulfonic acid bonded with two sulfonic acid groups, and naphthalene bonded with three sulfonic acid groups. Phenol trisulfonic acid. Specifically, 1-naphthol-2-sulfonic acid, 1-naphthol-4-sulfonic acid (NW acid), 1-naphthol-5-sulfonic acid (L acid), 1-naphthol-8-sulfonate Acid, 2-naphthol-1-sulfonic acid, 2-naphthol-6-sulfonic acid (Schiff's acid), 2-naphthol-8-sulfonic acid (saffronic acid), 1-naphthol-2,4 -disulfonic acid, 1-naphthol-3,6-disulfonic acid, 1-naphthol-3,8-disulfonic acid (ε acid), 2-naphthol-3,6-disulfonic acid (R acid ), 2-naphthol-3,8-disulfonic acid, 2-naphthol-6,8-disulfonic acid (G acid), 1-naphthol-2,4,7-trisulphonic acid, 1-naphthalene Phenol-3,6,8-trisulphonic acid (oxocochic acid), 2-naphthol-3,6,8-trisulphonic acid, and the like.
其中優選鍵結有2個磺酸基的萘二磺酸及萘酚二磺酸。其中優選1,5-萘二磺酸、2,7-萘二磺酸、2-萘酚-3,6-二磺酸、2-萘酚-3,8-二磺酸。 Among them, naphthalenedisulfonic acid and naphthol disulfonic acid having two sulfonic acid groups bonded thereto are preferred. Among them, preferred are 1,5-naphthalenedisulfonic acid, 2,7-naphthalene disulfonic acid, 2-naphthol-3,6-disulfonic acid, and 2-naphthol-3,8-disulfonic acid.
另外,包含維多利亞純藍BO(C.I.鹼性藍7)與萘二磺酸的成鹽化合物、包含維多利亞純藍BO(C.I.鹼性藍7)與萘酚二磺酸的成鹽化合物是優選的染料。 In addition, a salt-forming compound comprising Victoria Pure Blue BO (CI Basic Blue 7) and naphthalenedisulfonic acid, a salt-forming compound comprising Victoria Pure Blue BO (CI Basic Blue 7) and naphthol disulfonic acid is a preferred dye. .
使萘類的二磺化物、萘酚類的二磺化物與三芳基甲烷 類鹼性染料反應,製成本實施形態的著色組成物的[IV]著色劑的情況時,1莫耳的二磺化物相對於三芳基甲烷類染料2莫耳反應而成鹽。其中和了電荷,且以反離子成分的莫耳比計而言具有2倍量的著色劑成分,因此是成為作為著色劑而並不損及染料的顯色的優選成分。亦即,優選使用具有至少2個磺酸基的有機磺酸。 Disulfonates of naphthalenes, disulfides of naphthols and triarylmethane When the basic dye is reacted to form the [IV] coloring agent of the colored composition of the present embodiment, 1 mol of the disulfonate is reacted with the triarylmethane dye 2 to form a salt. Since the charge is contained and the colorant component is twice as large as the molar ratio of the counter ion component, it is a preferable component which does not impair the color development of the dye as a colorant. That is, it is preferred to use an organic sulfonic acid having at least 2 sulfonic acid groups.
而且,三芳基甲烷類鹼性染料與有機磺酸、(芳香族羥基羧酸)的成鹽化合物可通過先前已知的方法而合成。在日本專利特開2003-215850號公報等中揭示了具體的手法。 Further, a salt-forming compound of a triarylmethane-based basic dye and an organic sulfonic acid or (aromatic hydroxycarboxylic acid) can be synthesized by a previously known method. A specific method is disclosed in Japanese Laid-Open Patent Publication No. 2003-215850.
而且,可與上述有機磺酸同樣地使用芳香族羥基羧酸而獲得成鹽化合物。作為優選的芳香族羥基羧酸,其中優選使用3,5-二第三丁基水楊酸、3-羥基-2-萘甲酸、3-苯基水楊酸。在使用芳香族羥基羧酸的情況時,獲得三芳基甲烷類染料中的胺基(-NHC2H5)部分與芳香族羥基羧酸的羧酸(-COOH)部分鍵結而成的成鹽化合物。而且,羥基(-OH)與成鹽反應並無關類地殘存。 Further, an aromatic hydroxycarboxylic acid can be used in the same manner as the above organic sulfonic acid to obtain a salt-forming compound. As a preferred aromatic hydroxycarboxylic acid, 3,5-di-t-butylsalicylic acid, 3-hydroxy-2-naphthoic acid, and 3-phenylsalicylic acid are preferably used. In the case of using an aromatic hydroxycarboxylic acid, a salt formed by bonding an amine group (-NHC 2 H 5 ) moiety of a triarylmethane dye to a carboxylic acid (-COOH) moiety of an aromatic hydroxycarboxylic acid is obtained. Compound. Moreover, the hydroxyl group (-OH) remains unrelated to the salt formation reaction.
另外,包含維多利亞純藍BO(C.I.鹼性藍7)與3,5-二第三丁基水楊酸的成鹽化合物是優選的染料。 Further, a salt-forming compound comprising Victoria Pure Blue BO (C.I. Basic Blue 7) and 3,5-di-t-butylsalicylic acid is a preferred dye.
三芳基甲烷類染料的酸性染料優選使用食用藍101號(C.I.酸性藍1)、酸性純藍(C.I.酸性藍3)、色澱藍I(C.I.酸性藍5)、色澱藍II(C.I.酸性藍7)、食用藍1號(C.I.酸性藍9)、C.I.酸性藍22、C.I.酸性藍83、C.I.酸性藍90、C.I.酸性藍93、C.I.酸性藍100、C.I.酸性藍103、C.I.酸性 藍104、C.I.酸性藍109。 The acid dye of the triarylmethane dye is preferably Edible Blue No. 101 (CI Acid Blue 1), Acid Pure Blue (CI Acid Blue 3), Lake Blue I (CI Acid Blue 5), Lake Blue II (CI Acid Blue) 7), Edible Blue No. 1 (CI Acid Blue 9), CI Acid Blue 22, CI Acid Blue 83, CI Acid Blue 90, CI Acid Blue 93, CI Acid Blue 100, CI Acid Blue 103, CI Acid Blue 104, C.I. Acid Blue 109.
三芳基甲烷類酸性染料與季銨化合物的成鹽化合物可通過先前已知的方法而合成。 A salt forming compound of a triarylmethane acid dye and a quaternary ammonium compound can be synthesized by a previously known method.
若列舉一例,則將三芳基甲烷類酸性染料溶解於水中後,添加季銨化合物,一面進行攪拌一面進行成鹽化處理即可。此處,獲得三芳基甲烷類酸性染料中的磺酸基(-SO3H)部分與季銨化合物的銨基(NH4 +)部分鍵結而成的成鹽化合物。季銨化合物優選使用三乙基苄基氯化銨等。 As an example, after the triarylmethane acid dye is dissolved in water, the quaternary ammonium compound may be added and the salt formation treatment may be carried out while stirring. Here, a salt-forming compound obtained by bonding a sulfonic acid group (-SO 3 H) moiety in a triarylmethane-based acid dye to an ammonium group (NH 4 + ) moiety of a quaternary ammonium compound is obtained. As the quaternary ammonium compound, triethylbenzylammonium chloride or the like is preferably used.
在本實施形態中,可使用三芳基甲烷色澱顏料作為三芳基甲烷類著色劑。 In the present embodiment, a triarylmethane lake pigment can be used as the triarylmethane colorant.
顏料化中所進行的色澱化是利用沉澱劑而由可溶性的染料獲得不溶性鹽,是具有化學性反應,且染料成分吸附於沉澱劑粒子上的狀態。 The lake formation carried out in the pigmentation is a state in which a preservative salt is obtained from a soluble dye using a precipitating agent, and a chemical reaction is carried out, and the dye component is adsorbed on the precipitant particles.
三胺基三苯基甲烷類染料通過進行色澱化而改善耐候性、耐熱性,成為穩定的良好的著色劑。 The triaminotriphenylmethane dye is improved in weather resistance and heat resistance by performing lake formation, and is a stable and excellent color former.
用以對三芳基甲烷類染料進行色澱化的沉澱劑可列舉氯化鋇、氯化鈣、硫酸銨、氯化鋁、乙酸鋁、乙酸鉛、丹寧酸、卡他諾(Katanol)、被稱為絡合酸的複合雜多酸(磷鎢酸、磷鉬酸、磷鎢鉬酸、矽鎢鉬酸、矽鎢酸、矽鉬酸)等。其中,使用複合雜多酸的色澱顏料由於鮮明且著色力大、耐光性顯著提高,因此是優選的顏料。 Examples of the precipitating agent used for the lamination of the triarylmethane dye include barium chloride, calcium chloride, ammonium sulfate, aluminum chloride, aluminum acetate, lead acetate, tannic acid, katatan (Katanol), and A complex heteropoly acid (phosphoric acid, phosphomolybdic acid, phosphotungstic acid, samarium tungsten molybdate, samarium tungstic acid, samarium molybdate) called a complex acid. Among them, a lake pigment using a composite heteropoly acid is a preferred pigment because of its sharpness, large coloring power, and markedly improved light resistance.
三芳基甲烷類顏料具體可列舉C.I.顏料藍1、C.I.顏料藍2、C.I.顏料藍9、C.I.顏料藍10、C.I.顏料藍14、C.I.顏 料藍62、C.I.顏料紫3、C.I.顏料紫27、C.I.顏料紫39等。 Specific examples of the triarylmethane pigments include C.I. Pigment Blue 1, C.I. Pigment Blue 2, C.I. Pigment Blue 9, C.I. Pigment Blue 10, C.I. Pigment Blue 14, C.I. Blue 62, C.I. Pigment Violet 3, C.I. Pigment Violet 27, C.I. Pigment Violet 39 and the like.
若具體地列舉更優選的三芳基甲烷類顏料,則為:C.I.顏料藍1。 Specifically, a more preferable triarylmethane-based pigment is: C.I. Pigment Blue 1.
以磷鎢鉬酸對C.I.鹼性藍26、C.I.鹼性藍7進行色澱化。 The C.I. Basic Blue 26, C.I. Basic Blue 7 was subjected to lake formation with phosphotungstic acid.
C.I.顏料紫3。 C.I. Pigment Violet 3.
以磷鎢鉬酸對C.I.鹼性紫1進行色澱化。 The C.I. Basic Violet 1 was subjected to lake formation with phosphotungstic acid.
C.I.顏料紫39。 C.I. Pigment Violet 39.
以磷鎢鉬酸對C.I.鹼性紫3(結晶紫)進行色澱化。 The C.I. Basic Violet 3 (crystal violet) was subjected to lake formation with phosphotungstic acid.
其中優選使用C.I.顏料藍1。 Among them, C.I. Pigment Blue 1 is preferably used.
其次,作為優選的[IV]著色劑的例子的巴比妥酸偶氮類染料及吡啶酮偶氮類例如具有以下的結構。然而,本實施形態中所使用的巴比妥酸偶氮類染料及吡啶酮偶氮類並不限定於該些結構。 Next, as an example of a preferred [IV] coloring agent, a barbituric azo dye and a pyridone azo have the following structures, for example. However, the barbituric azo dye and the pyridone azo used in the present embodiment are not limited to these structures.
在式(101)中,T1及T2分別獨立地表示氧原子或硫原子。 In the formula (101), T 1 and T 2 each independently represent an oxygen atom or a sulfur atom.
R101~R104分別獨立地表示氫原子、亦可具有取代基 的碳數為1~10的脂肪族烴基、亦可具有取代基的碳數為6~20的芳基、亦可具有取代基的碳數為7~20的芳烷基或亦可具有取代基的碳數為2~10的醯基。 R 101 to R 104 each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, or a substituent. The aralkyl group having a carbon number of 7 to 20 or a fluorenyl group having a carbon number of 2 to 10 which may have a substituent.
R105~R112分別獨立地表示氫原子、碳數為1~10的脂肪族烴基、碳數為1~8的烷氧基、羧基、磺基、胺磺醯基或N位-取代胺磺醯基。上述脂肪族烴基中所含的氫原子亦可被鹵素原子取代。 R 105 to R 112 each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a carboxyl group, a sulfo group, an aminesulfonyl group or an N-substituted aminesulfonate.醯基. The hydrogen atom contained in the above aliphatic hydrocarbon group may be substituted by a halogen atom.
若加以更詳細的說明,則在式(101)中,R101~R104中的碳數為1~10的脂肪族烴基可以是直鏈狀、分支狀或環狀的任意種。碳數為1~10的脂肪族烴基的碳數優選為2~8,更優選為3~6。碳數為1~10的脂肪族烴基例如可列舉甲基、乙基、正丙基、異丙基、正丁基、異丁基、仲丁基、第三丁基、乙基己基(2-乙基己基等)、環戊基、環己基及環己基烷基等。 More specifically, in the formula (101), the aliphatic hydrocarbon group having 1 to 10 carbon atoms in R 101 to R 104 may be any of a linear chain, a branched chain or a cyclic group. The number of carbon atoms of the aliphatic hydrocarbon group having 1 to 10 carbon atoms is preferably 2 to 8, more preferably 3 to 6. Examples of the aliphatic hydrocarbon group having 1 to 10 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, ethylhexyl (2- Ethylhexyl or the like), cyclopentyl, cyclohexyl and cyclohexylalkyl groups.
而且,碳數為1~10的脂肪族烴基中所含的氫原子亦可被羥基、碳數為1~8的(優選碳數為1~4的)烷氧基或碳數為1~8的(優選碳數為1~4的)硫代烷氧基取代。經取代的脂肪族烴基例如可列舉羥基乙基(2-羥基乙基等)、乙氧基乙基(2-乙氧基乙基等)、乙基己氧基丙基(3-(2-乙基己氧基)丙基等)及甲硫基丙基(3-甲硫基丙基等)等。 Further, the hydrogen atom contained in the aliphatic hydrocarbon group having 1 to 10 carbon atoms may be a hydroxyl group or an alkoxy group having a carbon number of 1 to 8 (preferably having a carbon number of 1 to 4) or a carbon number of 1 to 8. (preferably having a carbon number of 1 to 4) substituted by a thioalkoxy group. Examples of the substituted aliphatic hydrocarbon group include a hydroxyethyl group (2-hydroxyethyl group, etc.), an ethoxyethyl group (2-ethoxyethyl group, etc.), and an ethylhexyloxypropyl group (3-(2-). Ethylhexyloxypropyl, etc.) and methylthiopropyl (3-methylthiopropyl, etc.) and the like.
R101~R104中的碳數為6~20的芳基可未經取代,亦可具有脂肪族烴基、烷氧基、羧基、磺基或包含酯鍵的基等取代基。所述芳基的碳數包含取代基的碳數而進行計 數,優選為6~10。芳基例如可列舉苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-磺苯基、3-磺苯基、4-磺苯基及乙氧基羰基苯基(4-(COOC2H5)Ph基(Ph基表示苯基)等)等。 The aryl group having 6 to 20 carbon atoms in R 101 to R 104 may be unsubstituted, and may have a substituent such as an aliphatic hydrocarbon group, an alkoxy group, a carboxyl group, a sulfo group or a group containing an ester bond. The carbon number of the aryl group is counted by the carbon number of the substituent, and is preferably 6 to 10. Examples of the aryl group include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 2-methoxyphenyl group, a 3-methoxyphenyl group, and a 4-methoxy group. A phenyl group, a 2-sulfophenyl group, a 3-sulfophenyl group, a 4-sulfophenyl group, and an ethoxycarbonylphenyl group (4-(COOC 2 H 5 )Ph group (Ph group represents a phenyl group), etc.).
R101~R104中的碳數為7~20的芳烷基的烷基部分可為直鏈狀、分支狀或環狀的任意種。芳烷基的碳數包含取代基的碳數而進行計數,優選為7~10。碳數為7~20的芳烷基可列舉苄基及苯乙基等。 The alkyl moiety of the aralkyl group having 7 to 20 carbon atoms in R 101 to R 104 may be any of a linear chain, a branched chain or a cyclic group. The carbon number of the aralkyl group is counted by the carbon number of the substituent, and is preferably 7 to 10. Examples of the aralkyl group having 7 to 20 carbon atoms include a benzyl group and a phenethyl group.
R101~R104中的碳數為2~10的醯基可未經取代,亦可鍵結脂肪族烴基或烷氧基等取代基。醯基的碳數包含取代基的碳數而進行計數,其個數優選為2~10。醯基例如可列舉乙醯基、苯甲醯基、甲氧基苯甲醯基(對甲氧基苯甲醯基等)等。 The fluorenyl group having 2 to 10 carbon atoms in R 101 to R 104 may be unsubstituted or may be bonded to a substituent such as an aliphatic hydrocarbon group or an alkoxy group. The carbon number of the mercapto group is counted by the carbon number of the substituent, and the number thereof is preferably 2 to 10. Examples of the mercapto group include an ethenyl group, a benzamidine group, a methoxybenzylidene group (p-methoxybenzylidene group, etc.).
R105~R112中的碳數為1~10的脂肪族烴基可列舉與R101~R104的情況下相同的基。R105~R112的脂肪族烴基中所含的氫原子亦可被鹵素原子取代,鹵素原子優選列舉氟原子。被鹵素原子取代的脂肪族烴基的具體例可列舉三氟甲基等。 The aliphatic hydrocarbon group having 1 to 10 carbon atoms in R 105 to R 112 may be the same as those in the case of R 101 to R 104 . The hydrogen atom contained in the aliphatic hydrocarbon group of R 105 to R 112 may be substituted by a halogen atom, and the halogen atom is preferably a fluorine atom. Specific examples of the aliphatic hydrocarbon group substituted with a halogen atom include a trifluoromethyl group and the like.
R105~R112中的碳數為1~8的烷氧基的碳數優選為1~4。烷氧基例如可列舉甲氧基、乙氧基、異丙氧基、正丙氧基、正丁氧基、異丁氧基、仲丁氧基及第三丁氧基等。 The number of carbon atoms of the alkoxy group having 1 to 8 carbon atoms in R 105 to R 112 is preferably 1 to 4. Examples of the alkoxy group include a methoxy group, an ethoxy group, an isopropoxy group, a n-propoxy group, a n-butoxy group, an isobutoxy group, a sec-butoxy group, and a third butoxy group.
R105~R112中的N位-取代胺磺醯基例如優選為N位-單取代胺磺醯基,以-SO2NHR140而表示。 The N-substituted sulfonyl group in R 105 to R 112 is, for example, preferably an N-substituted monosulfonylsulfonyl group, which is represented by -SO 2 NHR 140 .
-SO2NHR140中所含的R140表示亦可具有取代基的碳 數為1~10的脂肪族烴基、亦可具有取代基的碳數為6~20的芳基、亦可具有取代基的碳數為7~20的芳烷基或亦可具有取代基的碳數為2~10的醯基。 R 140 contained in -SO 2 NHR 140 represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, or a substituent. The aralkyl group having a carbon number of 7 to 20 or a fluorenyl group having a carbon number of 2 to 10 which may have a substituent.
R140中的碳數為1~10的脂肪族烴基可為直鏈狀、分支狀或環狀的任意種。脂肪族烴基的碳數並不包含取代基的碳數,其個數優選為6~10。 The aliphatic hydrocarbon group having 1 to 10 carbon atoms in R 140 may be any of a linear chain, a branched chain or a cyclic group. The carbon number of the aliphatic hydrocarbon group does not include the carbon number of the substituent, and the number thereof is preferably 6 to 10.
R140中的碳數為1~10的脂肪族烴基例如可列舉甲基、乙基、正丙基、異丙基、正丁基、異丁基、仲丁基、第三丁基、甲基丁基(1,1,3,3-四甲基丁基等)、甲基己基(1-甲基己基、1,5-二甲基己基等)、乙基己基(2-乙基己基等)、環戊基、環己基、甲基環己基(2-甲基環己基等)及環己基烷基等。 Examples of the aliphatic hydrocarbon group having 1 to 10 carbon atoms in R 140 include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methyl. Butyl (1,1,3,3-tetramethylbutyl, etc.), methylhexyl (1-methylhexyl, 1,5-dimethylhexyl, etc.), ethylhexyl (2-ethylhexyl, etc.) ), cyclopentyl, cyclohexyl, methylcyclohexyl (2-methylcyclohexyl, etc.) and cyclohexylalkyl.
-SO2NHR140中所含的R140中的碳數為1~10的脂肪族烴基亦可被碳數為1~8的(優選為碳數為1~4的)烷氧基取代,例如可列舉丙氧基丙基(3-(異丙氧基)丙基等)等。 The aliphatic hydrocarbon group having 1 to 10 carbon atoms in R 140 contained in -SO 2 NHR 140 may be substituted by an alkoxy group having 1 to 8 carbon atoms (preferably having 1 to 4 carbon atoms), for example, Examples thereof include a propoxypropyl group (3-(isopropoxy)propyl group, etc.).
R140中的碳數為6~20的芳基可未經取代,亦可具有脂肪族烴基或羥基等取代基。所述芳基的碳數包含取代基的碳數而進行計數,優選為6~10。芳基例如可列舉苯基、羥基苯基(4-羥基苯基等)、三氟甲基苯基(4-三氟甲基苯基等)等。 The aryl group having 6 to 20 carbon atoms in R 140 may be unsubstituted, and may have a substituent such as an aliphatic hydrocarbon group or a hydroxyl group. The carbon number of the aryl group is counted by the carbon number of the substituent, and is preferably 6 to 10. Examples of the aryl group include a phenyl group, a hydroxyphenyl group (such as a 4-hydroxyphenyl group), a trifluoromethylphenyl group (such as a 4-trifluoromethylphenyl group), and the like.
R140中的碳數為7~20的芳烷基的烷基部分可為直鏈狀或分支狀的任意種。芳烷基的碳數通常為7~20,優選為7~10。該芳烷基可列舉苄基、苯基丙基(1-甲基-3-苯 基丙基等)、苯基丁基(3-胺基-1-苯基丁基等)等苯基烷基等。 The alkyl moiety of the aralkyl group having 7 to 20 carbon atoms in R 140 may be any of a linear or branched form. The aralkyl group has a carbon number of usually 7 to 20, preferably 7 to 10. Examples of the aralkyl group include a phenyl group such as a benzyl group, a phenylpropyl group (1-methyl-3-phenylpropyl group), or a phenyl group such as a phenylbutyl group (3-amino-1-phenylbutyl group). Base.
R140中的碳數為2~10的醯基可未經取代,醯基中所含的氫原子亦可被脂肪族烴基或烷氧基取代。醯基的碳數包含取代基的碳數而進行計數,其個數優選為6~10。醯基例如可列舉乙醯基、苯甲醯基、鄰甲苯甲醯基、間甲苯甲醯基、對甲苯甲醯基及甲氧基苯甲醯基(對甲氧基苯甲醯基等)等。 The fluorenyl group having 2 to 10 carbon atoms in R 140 may be unsubstituted, and the hydrogen atom contained in the fluorenyl group may be substituted by an aliphatic hydrocarbon group or an alkoxy group. The carbon number of the mercapto group is counted by the carbon number of the substituent, and the number thereof is preferably 6 to 10. Examples of the mercapto group include an ethyl fluorenyl group, a benzamidine group, an o-tolylmethyl fluorenyl group, a m-tolylmethyl fluorenyl group, a p-tolyl fluorenyl group, and a methoxybenzyl fluorenyl group (p-methoxybenzyl fluorenyl group). Wait.
作為優選的[IV]著色劑的例子的吡啶酮偶氮類例如具有以下的結構。 The pyridone azo which is an example of a preferable [IV] coloring agent has the following structures, for example.
在式(102)中,Z表示鹵素原子,亦可具有取代基的碳數為1~12的脂肪族烴基,碳數為1~8的烷氧基,具有1個或2個選自由羥基、羧基、胺甲醯基、磺基、胺磺醯基及N位-取代胺磺醯基所構成的群組的至少1種取代基的苯基,或者具有1個~3個選自由鹵素原子、亦可具有取代基的碳數為1~12的脂肪族烴基、碳數為1~8的烷氧基、羥基、羧基、胺甲醯基、磺基、胺磺醯基及N位-取代胺磺醯基所構成的群組的至少1種取代基的萘基。 In the formula (102), Z represents a halogen atom, may have a substituent having an aliphatic hydrocarbon group having 1 to 12 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and having 1 or 2 selected from a hydroxyl group. a phenyl group having at least one substituent of a group consisting of a carboxyl group, an amine methyl sulfonyl group, a sulfo group, an amine sulfonyl group, and an N-substituted amine sulfonyl group, or having one to three selected from a halogen atom, An aliphatic hydrocarbon group having a carbon number of 1 to 12, an alkoxy group having 1 to 8 carbon atoms, a hydroxyl group, a carboxyl group, an aminomethyl sulfonyl group, a sulfo group, an amine sulfonyl group, and an N-substituted amine. A naphthyl group having at least one substituent of the group consisting of sulfonyl groups.
R121表示氫原子,直鏈狀、分支狀或環狀的碳數為1~10的脂肪族烴基、羧基或三氟甲基。 R 121 represents a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 10 carbon atoms, a carboxyl group or a trifluoromethyl group.
R122表示氫原子、氰基、胺甲醯基、N位-取代胺甲醯基、胺磺醯基或磺基。 R 122 represents a hydrogen atom, a cyano group, an amine carbenyl group, an N-substituted amine carbenyl group, an amine sulfonyl group or a sulfo group.
R123表示氫原子,亦可具有取代基的碳數為1~10的直鏈狀、分支狀或環狀的脂肪族烴基,亦可具有取代基的碳數為6~30的芳基,亦可具有取代基的碳數為7~20的芳烷基,亦可具有取代基的碳數為3~20的雜環基,胺甲醯基,N位-取代胺甲醯基,亦可具有取代基的碳數為2~20的烷氧基羰基,亦可具有取代基的碳數為7~30的芳氧基羰基,亦可具有取代基的碳數為2~20的醯基,亦可具有取代基的碳數為1~30的脂肪族磺醯基或亦可具有取代基的碳數為6~30的芳基磺醯基。 R 123 represents a hydrogen atom, and may have a linear, branched or cyclic aliphatic hydrocarbon group having a carbon number of 1 to 10, or a aryl group having a carbon number of 6 to 30, which may have a substituent. An aralkyl group having 7 to 20 carbon atoms which may have a substituent, a heterocyclic group having 3 to 20 carbon atoms which may have a substituent, an amine carbenyl group, an N-substituted amine carbenyl group, or The alkoxycarbonyl group having 2 to 20 carbon atoms of the substituent may have an aryloxycarbonyl group having 7 to 30 carbon atoms as a substituent, or a fluorenyl group having 2 to 20 carbon atoms having a substituent. An aliphatic sulfonyl group having 1 to 30 carbon atoms which may have a substituent or an arylsulfonyl group having 6 to 30 carbon atoms which may have a substituent.
若加以更詳細的說明,則在式(102)中,Z中的碳數為1~12的脂肪族烴基可為直鏈狀、分支鏈狀或環狀的任意種。脂肪族烴基的碳數包括所有的取代基的碳數,其個數通常為1~12,優選為2~11。脂肪族烴基例如可列舉正辛基、甲基己基(1,5-二甲基己基等)、乙基己基(2-乙基己基等)、環辛基、甲基環己基(2,2-二甲基環己基等)及環己基烷基等。脂肪族烴基中所含的氫原子亦可被碳數為1~8的烷氧基或羧基取代。具有取代基的脂肪族烴基可列舉烷氧基丙基(3-(2'-乙基己氧基)丙基等)及8-(羧基)辛基等。 More specifically, in the formula (102), the aliphatic hydrocarbon group having 1 to 12 carbon atoms in Z may be any of a linear chain, a branched chain or a cyclic group. The carbon number of the aliphatic hydrocarbon group includes the carbon number of all the substituents, and the number thereof is usually from 1 to 12, preferably from 2 to 11. Examples of the aliphatic hydrocarbon group include n-octyl group, methylhexyl group (1,5-dimethylhexyl group, etc.), ethylhexyl group (2-ethylhexyl group, etc.), cyclooctyl group, and methylcyclohexyl group (2,2- Dimethylcyclohexyl or the like) and cyclohexylalkyl group. The hydrogen atom contained in the aliphatic hydrocarbon group may be substituted by an alkoxy group having 1 to 8 carbon atoms or a carboxyl group. Examples of the aliphatic hydrocarbon group having a substituent include an alkoxypropyl group (3-(2'-ethylhexyloxy)propyl group) and an 8-(carboxy)octyl group.
Z中的碳數為1~8的烷氧基例如可列舉甲氧基、乙氧 基、異丙氧基、正丙氧基、正丁氧基、異丁氧基、仲丁氧基及第三丁氧基等。 Examples of the alkoxy group having 1 to 8 carbon atoms in Z include methoxy group and ethoxy group. Base, isopropoxy, n-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy.
Z中的鹵素原子可列舉氟原子、溴原子、氯原子及碘原子。 Examples of the halogen atom in Z include a fluorine atom, a bromine atom, a chlorine atom, and an iodine atom.
Z中的N位-取代胺磺醯基以-SO2N(R141)R142而表示。R141及R142分別獨立地表示氫原子、亦可具有取代基的碳數為1~16的脂肪族烴基、亦可具有取代基的碳數為6~20的芳基、亦可具有取代基的碳數為7~20的芳烷基或亦可具有取代基的碳數為2~15的醯基(其中,R141及R142並不同時為氫原子)。 The N-substituted sulfonyl group in Z is represented by -SO 2 N(R 141 )R 142 . R 141 and R 142 each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 16 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, or a substituent. The aralkyl group having a carbon number of 7 to 20 or a fluorenyl group having a carbon number of 2 to 15 which may have a substituent (wherein R 141 and R 142 are not simultaneously a hydrogen atom).
碳數為1~16的脂肪族烴基可為直鏈狀、分支狀或環狀的任意種,脂肪族烴基的碳數優選為6~16。 The aliphatic hydrocarbon group having 1 to 16 carbon atoms may be any of a linear chain, a branched chain or a cyclic group, and the aliphatic hydrocarbon group preferably has 6 to 16 carbon atoms.
R141及R142中的碳數為1~16的脂肪族烴基可為直鏈狀、分支鏈狀或環狀的任意種。脂肪族烴基的碳數並不包含取代基的碳數,其個數通常為1~16,優選為6~10。脂肪族烴基例如可列舉甲基、乙基、正丙基、異丙基、正丁基、異丁基、仲丁基、第三丁基、甲基丁基(1,1,3,3-四甲基丁基等)、甲基己基(1,5-二甲基己基等)、乙基己基(2-乙基己基等)、環戊基、環己基、甲基環己基(2-甲基環己基等)及環己基烷基等。脂肪族烴基中所含的氫原子亦可被碳數為1~8的烷氧基或羧基取代。具有取代基的脂肪族烴基可列舉丙氧基丙基(3-(異丙氧基)丙基等)、2-(羧基)乙基、3-(羧基)乙基及4-羧基乙基等。 The aliphatic hydrocarbon group having 1 to 16 carbon atoms in R 141 and R 142 may be any of a linear chain, a branched chain or a cyclic group. The carbon number of the aliphatic hydrocarbon group does not include the carbon number of the substituent, and the number thereof is usually from 1 to 16, preferably from 6 to 10. Examples of the aliphatic hydrocarbon group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methylbutyl (1,1,3,3- Tetramethylbutyl or the like), methylhexyl (1,5-dimethylhexyl, etc.), ethylhexyl (2-ethylhexyl, etc.), cyclopentyl, cyclohexyl, methylcyclohexyl (2-A) Alkylcyclohexyl or the like) and a cyclohexylalkyl group. The hydrogen atom contained in the aliphatic hydrocarbon group may be substituted by an alkoxy group having 1 to 8 carbon atoms or a carboxyl group. Examples of the aliphatic hydrocarbon group having a substituent include a propoxypropyl group (3-(isopropoxy)propyl group, etc.), a 2-(carboxy)ethyl group, a 3-(carboxy)ethyl group, a 4-carboxyethyl group, and the like. .
R141及R142中的碳數為6~20的芳基亦可具有脂肪族 烴基或羥基等取代基。芳基的碳數包含取代基的碳數而進行計數,通常為6~20,優選為6~10。芳基可列舉苯基、羧基苯基(2-羧基苯基、2,4-二羧基苯基等)、羥基苯基(4-羥基苯基等)、三氟甲基苯基(4-三氟甲基苯基等)及甲氧基苯基(4-甲氧基苯基)等。 The aryl group having 6 to 20 carbon atoms in R 141 and R 142 may have a substituent such as an aliphatic hydrocarbon group or a hydroxyl group. The carbon number of the aryl group is counted by the carbon number of the substituent, and is usually 6 to 20, preferably 6 to 10. Examples of the aryl group include a phenyl group, a carboxyphenyl group (2-carboxyphenyl group, a 2,4-dicarboxyphenyl group, etc.), a hydroxyphenyl group (4-hydroxyphenyl group, etc.), and a trifluoromethylphenyl group (4-three). Fluoromethylphenyl or the like) and methoxyphenyl (4-methoxyphenyl) and the like.
R141及R142中的碳數為7~20的芳烷基的烷基部分可為直鏈狀或分支狀的任意種。芳烷基的碳數通常為7~20,優選為7~10。芳烷基可列舉苄基、苯基乙基(2-苯基乙基、2-(4-羥基苯基)乙基等)、苯基乙撐(2-苯基乙撐等)、苯基丙基(1-甲基-3-苯基丙基等)及苯基丁基(3-胺基-1-苯基丁基等)等苯基烷基。 The alkyl moiety of the aralkyl group having 7 to 20 carbon atoms in R 141 and R 142 may be any of a linear or branched form. The aralkyl group has a carbon number of usually 7 to 20, preferably 7 to 10. Examples of the aralkyl group include a benzyl group, a phenylethyl group (2-phenylethyl group, a 2-(4-hydroxyphenyl)ethyl group, etc.), a phenylethylene group (2-phenylethylene group, etc.), and a phenyl group. A phenylalkyl group such as a propyl group (1-methyl-3-phenylpropyl group or the like) or a phenylbutyl group (3-amino-1-phenylbutyl group or the like).
R141及R142中的碳數為2~15的醯基可未經取代,亦可具有脂肪族烴基、烷氧基或羧基等取代基。醯基的碳數包含取代基的碳數而進行計數,其個數通常為2~15,優選為6~10。醯基例如可列舉乙醯基、苯甲醯基、甲氧基苯甲醯基(對甲氧基苯甲醯基等)、羧基乙醯基、2-羧基丙醯基、3-羧基丙醯基、2-羧基丁醯基、3-羧基丁醯基及4-羧基丁醯基等。 The fluorenyl group having 2 to 15 carbon atoms in R 141 and R 142 may be unsubstituted, and may have a substituent such as an aliphatic hydrocarbon group, an alkoxy group or a carboxyl group. The carbon number of the mercapto group is counted by the carbon number of the substituent, and the number thereof is usually 2 to 15, preferably 6 to 10. Examples of the mercapto group include an ethyl fluorenyl group, a benzamidine group, a methoxybenzylidene group (p-methoxybenzylidene group, etc.), a carboxyethyl group, a 2-carboxypropyl group, and a 3-carboxypropene group. A group, a 2-carboxybutanyl group, a 3-carboxybutanyl group, a 4-carboxybutanyl group, and the like.
R121表示氫原子,直鏈狀、分支狀或環狀的碳數為1~10的脂肪族烴基,羧基或三氟甲基。 R 121 represents a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 10 carbon atoms, a carboxyl group or a trifluoromethyl group.
R121中的碳數為1~10的脂肪族烴基的碳數並不包含取代基的碳數。其碳數優選為2~8,更優選為3~6。脂肪族烴基可列舉甲基、乙基、正丙基、異丙基、正丁基、異丁基、仲丁基、第三丁基、環戊基及環己基等。 The carbon number of the aliphatic hydrocarbon group having 1 to 10 carbon atoms in R 121 does not include the carbon number of the substituent. The carbon number is preferably 2 to 8, more preferably 3 to 6. Examples of the aliphatic hydrocarbon group include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a cyclopentyl group, and a cyclohexyl group.
R122表示氫原子、氰基、胺甲醯基或N位-取代胺甲醯基、胺磺醯基或磺基。 R 122 represents a hydrogen atom, a cyano group, an amine carbenyl group or an N-substituted amine carbenyl group, an amine sulfonyl group or a sulfo group.
R122中的N位-取代胺甲醯基可列舉-CON(R143)R144。R143及R144分別獨立表示氫原子、亦可具有取代基的碳數為1~10的脂肪族烴基、亦可具有取代基的碳數為6~20的芳基、亦可具有取代基的碳數為7~20的芳烷基或亦可具有取代基的碳數為2~10的醯基。 The N-substituted aminemethanyl group in R 122 may be -CON(R 143 )R 144 . R 143 and R 144 each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, or a substituent. An aralkyl group having 7 to 20 carbon atoms or a fluorenyl group having 2 to 10 carbon atoms which may have a substituent.
R143及R144的脂肪族烴基、芳基、芳烷基及醯基的說明及具體例與前述的R141及R142相同。其中,醯基亦可具有鹵素原子。亦可具有鹵素原子的醯基例如可列舉溴苯甲醯基(對溴苯甲醯基等)等。 The description and specific examples of the aliphatic hydrocarbon group, the aryl group, the aralkyl group and the fluorenyl group of R 143 and R 144 are the same as those of the above R 141 and R 142 . Among them, the fluorenyl group may have a halogen atom. Examples of the thiol group which may have a halogen atom include a bromobenzylidene group (p-bromobenzylidene group, etc.).
R123表示氫原子,亦可具有取代基的碳數為1~10的直鏈狀、分支狀或環狀的脂肪族烴基,亦可具有取代基的碳數為6~30的芳基,亦可具有取代基的碳數為7~20的芳烷基,亦可具有取代基的碳數為3~20的雜環基,胺甲醯基,N位-取代胺甲醯基,亦可具有取代基的碳數為2~20的烷氧基羰基,亦可具有取代基的碳數為7~30的芳氧基羰基,亦可具有取代基的碳數為2~20的醯基,亦可具有取代基的碳數為1~30的脂肪族磺醯基或亦可具有取代基的碳數為6~30的芳基磺醯基。 R 123 represents a hydrogen atom, and may have a linear, branched or cyclic aliphatic hydrocarbon group having a carbon number of 1 to 10, or a aryl group having a carbon number of 6 to 30, which may have a substituent. An aralkyl group having 7 to 20 carbon atoms which may have a substituent, a heterocyclic group having 3 to 20 carbon atoms which may have a substituent, an amine carbenyl group, an N-substituted amine carbenyl group, or The alkoxycarbonyl group having 2 to 20 carbon atoms of the substituent may have an aryloxycarbonyl group having 7 to 30 carbon atoms as a substituent, or a fluorenyl group having 2 to 20 carbon atoms having a substituent. An aliphatic sulfonyl group having 1 to 30 carbon atoms which may have a substituent or an arylsulfonyl group having 6 to 30 carbon atoms which may have a substituent.
R123中的脂肪族烴基可列舉與上述R121中的脂肪族烴基相同的基。 The aliphatic hydrocarbon group in R 123 may be the same one as the aliphatic hydrocarbon group in the above R 121 .
作為R123中的芳基,碳數通常為6~30,優選為6~20,更優選為6~16。芳基的具體例可列舉苯基、4-硝基 苯基、2-硝基苯基、2-氯苯基、2,4-二氯苯基、2,4-二甲基苯基、2-甲基苯基、4-甲氧基苯基、2-甲氧基苯基及2-甲氧基羰基-4-硝基苯基等。 The aryl group in R 123 has a carbon number of usually 6 to 30, preferably 6 to 20, and more preferably 6 to 16. Specific examples of the aryl group include a phenyl group, a 4-nitrophenyl group, a 2-nitrophenyl group, a 2-chlorophenyl group, a 2,4-dichlorophenyl group, a 2,4-dimethylphenyl group, and 2 -methylphenyl, 4-methoxyphenyl, 2-methoxyphenyl, 2-methoxycarbonyl-4-nitrophenyl, and the like.
R123中的芳烷基可為直鏈狀或分支狀的任意種,碳數優選為7~10。芳烷基的具體例可列舉苄基、苯基丙基(1-甲基-3-苯基丙基等)及苯基丁基(3-胺基-1-苯基丁基等)等苯基烷基。 The aralkyl group in R 123 may be any of a linear or branched form, and the number of carbon atoms is preferably 7 to 10. Specific examples of the aralkyl group include benzyl, phenylpropyl (1-methyl-3-phenylpropyl, etc.), and phenylbutyl (3-amino-1-phenylbutyl) and the like. Alkyl group.
R123中的碳數為3~20的雜環基可飽和亦可不飽和,碳數優選為3~20,更優選為5~15。雜環基的具體例可列舉吡唑基、1,2,4-三唑基、異噻唑基、苯並異噻唑基、噻唑基、苯並噻唑基、噁唑基及1,2,4-噻二唑基等。而且,亦可進一步具有取代基。 The heterocyclic group having 3 to 20 carbon atoms in R 123 may be saturated or unsaturated, and the carbon number is preferably 3 to 20, and more preferably 5 to 15. Specific examples of the heterocyclic group include pyrazolyl, 1,2,4-triazolyl, isothiazolyl, benzisothiazolyl, thiazolyl, benzothiazolyl, oxazolyl, and 1,2,4-. Thiadiazolyl and the like. Further, it may further have a substituent.
R123中的N位-取代胺甲醯基與關於R122而所述的N位-取代胺甲醯基相同。 The N-substituted amine indenyl group in R 123 is the same as the N-substituted amine indenyl group described for R 122 .
R123中的烷氧基羰基可未經取代亦可具有取代基,亦可為環狀。烷氧基羰基的碳數通常為2~20,優選為2~16,更優選為2~10。烷氧基羰基可列舉甲氧基羰基、乙氧基羰基及丁氧基羰基等。 The alkoxycarbonyl group in R 123 may be unsubstituted or may have a substituent or may be cyclic. The alkoxycarbonyl group has a carbon number of usually 2 to 20, preferably 2 to 16, more preferably 2 to 10. The alkoxycarbonyl group may, for example, be a methoxycarbonyl group, an ethoxycarbonyl group or a butoxycarbonyl group.
R123中的芳氧基羰基可未經取代亦可具有取代基,碳數通常為7~30,優選為7~20,更優選為7~16。芳氧基羰基可列舉苯氧基羰基及4-甲基苯氧基羰基等。 The aryloxycarbonyl group in R 123 may be unsubstituted or have a substituent, and the carbon number is usually from 7 to 30, preferably from 7 to 20, more preferably from 7 to 16. Examples of the aryloxycarbonyl group include a phenoxycarbonyl group and a 4-methylphenoxycarbonyl group.
R123中的醯基可為脂肪族羰基亦可為芳基羰基,且可為飽和或不飽和的任意種,亦可為環狀,亦可進一步具有取代基。碳數通常為2~20,優選為2~15,更優選為2~ 10。醯基可列舉乙醯基、丙醯基、丁醯基、異丁醯基、戊醯基、異戊醯基、特戊醯基、苯甲醯基等。 The mercapto group in R 123 may be an aliphatic carbonyl group or an arylcarbonyl group, and may be any of saturated or unsaturated, may be cyclic, or may further have a substituent. The carbon number is usually 2 to 20, preferably 2 to 15, more preferably 2 to 10. Examples of the fluorenyl group include an ethyl group, a propyl group, a butyl group, an isobutyl group, a pentamidine group, an isopentenyl group, a pentamidine group, a benzamidine group and the like.
R123中的脂肪族磺醯基可飽和亦可不飽和,亦可為環狀。碳數通常為1~30,優選為1~20,更優選為1~16。脂肪族磺醯基可列舉甲磺醯基、丁磺醯基、甲氧基甲磺醯基、甲氧基乙磺醯基及乙氧基乙磺醯基等。 The aliphatic sulfonyl group in R 123 may be saturated or unsaturated, or may be cyclic. The carbon number is usually from 1 to 30, preferably from 1 to 20, and more preferably from 1 to 16. Examples of the aliphatic sulfonyl group include a methylsulfonyl group, a butyl sulfonyl group, a methoxymethylsulfonyl group, a methoxyethanesulfonyl group, and an ethoxyethanesulfonyl group.
R123中的芳基磺醯基亦可具有取代基,碳數通常為6~30,優選為6~20,更優選為6~18。芳基磺醯基可列舉苯磺醯基及甲苯磺醯基等。 The arylsulfonyl group in R 123 may have a substituent, and the carbon number is usually from 6 to 30, preferably from 6 to 20, more preferably from 6 to 18. Examples of the arylsulfonyl group include a benzenesulfonyl group and a toluenesulfonyl group.
其次,作為優選的[IV]著色劑的例子的二酮基吡咯並吡咯類及酞菁類例如具有以下的結構。但本實施形態中所使用的二酮基吡咯並吡咯類及酞菁類著色劑並不僅限於該些。 Next, the diketopyrrolopyrroles and phthalocyanines which are examples of preferred [IV] colorants have the following structures, for example. However, the diketopyrrolopyrrole and phthalocyanine coloring agents used in the present embodiment are not limited thereto.
在式(103)中,Y表示氧原子或硫原子。R131與R132可相同亦可不同,表示氫原子、烷基、環烷基、烯基、炔基、芳基、芳烷基、胺甲醯基、烷基胺甲醯基、芳基胺甲醯基、或烷氧基羰基。R133、R134可相同亦可不同,表示 烷基、環烷基、芳烷基、或者碳環或雜環式芳香族殘基。 In the formula (103), Y represents an oxygen atom or a sulfur atom. R 131 and R 132 may be the same or different and represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, an aralkyl group, an amine carbaryl group, an alkylamine carbaryl group, an arylamine. Mercapto, or alkoxycarbonyl. R 133 and R 134 may be the same or different and each represents an alkyl group, a cycloalkyl group, an aralkyl group, or a carbocyclic or heterocyclic aromatic residue.
若加以更詳細的說明,則在式(103)中,R131、R132、R133及R134中的烷基可分支亦可不分支,優選具有優選為1個~18個,更優選為1個~12個、特別優選為1個~6個的碳原子。具體而言可列舉甲基、乙基、異丙基、仲丁基、第三丁基、第三戊基、辛基、癸基、十二烷基或十八烷基等。 More specifically, in the formula (103), the alkyl groups in R 131 , R 132 , R 133 and R 134 may or may not be branched, and preferably have from 1 to 18, more preferably 1 One to twelve, particularly preferably one to six carbon atoms. Specific examples thereof include a methyl group, an ethyl group, an isopropyl group, a sec-butyl group, a tert-butyl group, a third pentyl group, an octyl group, a decyl group, a dodecyl group or an octadecyl group.
R131、R132、R133及R134中的環烷基優選具有優選為3個~8個、更優選為3個~6個的碳原子,具體而言可列舉環戊基、環己基等。R131、R132中的烯基優選具有優選為2個~8個、更優選為2個~6個的碳原子,具體而言可列舉乙烯基、烯丙基等。R131、R132中的炔基優選具有優選為2個~8個、更優選為2個~6個的碳原子,具體而言可列舉乙炔基等。 The cycloalkyl group in R 131 , R 132 , R 133 and R 134 preferably has 3 to 8 carbon atoms, more preferably 3 to 6 carbon atoms, and specific examples thereof include a cyclopentyl group and a cyclohexyl group. . The alkenyl group in R 131 and R 132 preferably has 2 to 8 carbon atoms, more preferably 2 to 6 carbon atoms, and specific examples thereof include a vinyl group and an allyl group. The alkynyl group in R 131 and R 132 preferably has 2 to 8 carbon atoms, more preferably 2 to 6 carbon atoms, and specific examples thereof include an ethynyl group.
R131、R132中的芳基優選具有優選為6個~10個的碳原子,具體而言可列舉苯基、萘基等。R131、R132中的烷基胺甲醯基的烷基可列舉與上述烷基相同的烷基。R131、R132中的芳基胺甲醯基的芳基可列舉與上述芳基相同的芳基。R131、R132中的烷氧基羰基的烷氧基可列舉碳數為1個~4個的烷氧基,具體而言可列舉甲氧基、乙氧基、丁氧基等。 The aryl group in R 131 and R 132 preferably has 6 to 10 carbon atoms, and specific examples thereof include a phenyl group and a naphthyl group. The alkyl group of the alkylaminecarbamyl group in R 131 and R 132 may be the same alkyl group as the above alkyl group. The aryl group of the arylaminecarbamyl group in R 131 and R 132 may be the same aryl group as the above aryl group. Examples of the alkoxy group of the alkoxycarbonyl group in R 131 and R 132 include alkoxy groups having 1 to 4 carbon atoms, and specific examples thereof include a methoxy group, an ethoxy group, and a butoxy group.
在式(103)中,R131、R132、R133及R134表示芳烷基的情況下,特別優選含有單環~三環式、更優選為單環式或二環式的芳基殘基。具體而言例如可列舉苄基及苯基乙 基。在式(103)中,當R133及R134表示碳環式芳香族殘基的情況時,適宜的是單環~四環式、特別是單環式或二環式的殘基,亦即苯基、聯苯基或萘基。 In the formula (103), when R 131 , R 132 , R 133 and R 134 represent an aralkyl group, it is particularly preferred to contain a monocyclic to tricyclic formula, more preferably a monocyclic or bicyclic aryl residue. base. Specific examples thereof include a benzyl group and a phenylethyl group. In the formula (103), when R 133 and R 134 represent a carbocyclic aromatic residue, a monocyclic to tetracyclic ring, particularly a monocyclic or bicyclic residue, that is, Phenyl, biphenyl or naphthyl.
在式(103)中,R133及R134表示雜環式芳香族殘基的情況下,適宜的是單環~三環式的殘基。該些基可為純雜環式,而且亦可含有1個雜環及1個或多個縮合苯環,具體而言例如可列舉吡啶基、嘧啶基、吡嗪基、三嗪基、呋喃基、吡咯基、噻吩基、喹啉基、香豆素基、苯並呋喃基、苯並咪唑基或苯並噁唑基等。 In the formula (103), when R 133 and R 134 represent a heterocyclic aromatic residue, a monocyclic to tricyclic residue is suitable. These groups may be a pure heterocyclic ring type, and may also contain one heterocyclic ring and one or more condensed benzene rings, and specific examples thereof include a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, and a furyl group. , pyrrolyl, thienyl, quinolyl, coumarinyl, benzofuranyl, benzimidazolyl or benzoxazolyl and the like.
在式(103)中,R131、R132優選為氫原子。而且,R133、R134優選分別獨立為碳數為1個~4個的烷基、二烷基胺基、鹵烷基或亦可具有鹵素原子作為取代基的苯基。 In the formula (103), R 131 and R 132 are preferably a hydrogen atom. Further, R 133 and R 134 are each preferably an alkyl group having 1 to 4 carbon atoms, a dialkylamino group, a haloalkyl group or a phenyl group which may have a halogen atom as a substituent.
其次,作為優選的[IV]著色劑的例子的酞菁類著色劑優選的是鹵化鋅酞菁類著色劑,例如具有以下的結構。 Next, a phthalocyanine coloring agent which is an example of a preferred [IV] coloring agent is preferably a zinc halide phthalocyanine coloring agent, and has the following structure, for example.
在式(104)中,X1~X16分別獨立地表示氫原子、氯原子或溴原子。 In the formula (104), X 1 to X 16 each independently represent a hydrogen atom, a chlorine atom or a bromine atom.
更詳細而言,在式(104)中,X1~X16所表示的取代基的個數優選為氯原子為0個~6個,溴原子為10個~16個,且氯原子與溴原子的和為10個~16個;更優選為氯原子為0個~3個、溴原子為13個~16個,且氯原子與溴原子的和為13個~16個;進一步更優選為氯原子為1個~3個、溴原子為13個~15個,且氯原子與溴原子的和為14個~16個。 More specifically, in the formula (104), the number of the substituents represented by X 1 to X 16 is preferably from 0 to 6 in the chlorine atom, from 10 to 16 in the bromine atom, and the chlorine atom and the bromine. The sum of atoms is 10 to 16; more preferably 0 to 3 chlorine atoms, 13 to 16 bromine atoms, and 13 to 16 chlorine atoms and bromine atoms; further more preferably The chlorine atom is 1 to 3, the bromine atom is 13 to 15, and the sum of the chlorine atom and the bromine atom is 14 to 16.
其次,關於可於[IV]著色劑中使用的無機顏料,例如可列舉氧化鈦、硫酸鋇、碳酸鈣、鋅白、硫酸鉛、鉻黃、鋅黃、鐵丹(紅色氧化鐵(III))、鎘紅、群青、普魯士藍、氧化鉻綠、鈷綠、棕土、鈦黑、合成鐵黑、碳黑等。 Next, examples of the inorganic pigment which can be used in the [IV] coloring agent include titanium oxide, barium sulfate, calcium carbonate, zinc white, lead sulfate, chrome yellow, zinc yellow, and iron oxide (red iron oxide (III)). , cadmium red, ultramarine blue, Prussian blue, chrome oxide green, cobalt green, brown soil, titanium black, synthetic iron black, carbon black and so on.
其次,對著色組成物中所含有的[IV]著色劑的含量加以說明。 Next, the content of the [IV] coloring agent contained in the colored composition will be described.
作為[IV]著色劑的含量,相對於[I]鹼溶性樹脂100質量份而言優選為1質量份~400質量份,更優選為5質量份~350質量份。通過使[IV]著色劑的含量為上述範圍,能夠以高的水準而平衡性良好地達成著色組成物的鹼顯影性、像素的耐熱性、耐溶劑性以及作為著色圖案及彩色濾光片的高亮度化或高對比度化。 The content of the [IV] coloring agent is preferably 1 part by mass to 400 parts by mass, more preferably 5 parts by mass to 350 parts by mass, per 100 parts by mass of the [I] alkali-soluble resin. When the content of the [IV] coloring agent is in the above range, the alkali developability of the coloring composition, the heat resistance of the pixel, the solvent resistance, and the coloring pattern and the color filter can be achieved with good balance at a high level. High brightness or high contrast.
本實施形態的彩色濾光片的製造中所使用的本實施形態的著色組成物可含有[V]化合物。[V]化合物是起到作 為硬化劑的功能的化合物。因此,有時將其稱為[V]硬化劑。 The colored composition of the present embodiment used in the production of the color filter of the present embodiment may contain a [V] compound. [V] compound is a masterpiece A compound that functions as a hardener. Therefore, it is sometimes referred to as a [V] hardener.
[V]化合物是選自由下述式(1)所表示的化合物、下述式(2)所表示的化合物、三級胺化合物、胺鹽、鏻鹽、脒鹽、醯胺化合物、硫醇化合物、嵌段異氰酸酯化合物及含有咪唑環的化合物所構成的群組的至少1種化合物。著色組成物可通過含有選自該特定化合物群組的[V]化合物而實現著色圖案的低溫硬化。而且,亦可使著色組成物的保存穩定性提高。以下,對各化合物加以詳述。 The compound [V] is a compound represented by the following formula (1), a compound represented by the following formula (2), a tertiary amine compound, an amine salt, a phosphonium salt, a phosphonium salt, a guanamine compound, a thiol compound. At least one compound of the group consisting of a blocked isocyanate compound and a compound containing an imidazole ring. The colored composition can achieve low temperature hardening of the colored pattern by containing a compound of [V] selected from the group of the specific compounds. Moreover, the storage stability of the colored composition can also be improved. Hereinafter, each compound will be described in detail.
[式(1)及式(2)所表示的化合物] [Compounds represented by formula (1) and formula (2)]
[V]化合物優選為選自由上述式(1)及式(2)所表示的化合物所構成的群組的至少1種化合物。作為[V]化合物,可通過選擇具有胺基與缺電子基的上述特定化合物而實現著色圖案的低溫硬化。而且,亦可使著色組成物的保存穩定性提高。可進一步提高使用所得的彩色濾光片的液晶顯示元件的電壓保持率。 The compound [V] is preferably at least one compound selected from the group consisting of the compounds represented by the above formulas (1) and (2). As the [V] compound, low-temperature hardening of the colored pattern can be achieved by selecting the above specific compound having an amine group and an electron-deficient group. Moreover, the storage stability of the colored composition can also be improved. The voltage holding ratio of the liquid crystal display element using the obtained color filter can be further improved.
在式(1)中,R1~R6分別獨立為氫原子、吸電子基或胺基。其中,R1~R6中的至少1個是吸電子基,且R1~R6中的至少1個是胺基,上述胺基的氫原子的全部或一部分亦可被碳數為1~6的烷基取代,上述胺基的氫原子的全部或一部分也可以被碳數為1~6的烷基取代。 In the formula (1), R 1 to R 6 each independently represent a hydrogen atom, an electron withdrawing group or an amine group. Wherein at least one of R 1 to R 6 is an electron withdrawing group, and at least one of R 1 to R 6 is an amine group, and all or a part of the hydrogen atom of the amine group may be a carbon number of 1~ The alkyl group of 6 may be substituted with all or a part of the hydrogen atom of the above amine group by an alkyl group having 1 to 6 carbon atoms.
在上述式(2)中,R7~R16分別獨立為氫原子、吸電子基或胺基。其中,R7~R16中的至少1個是胺基。而且,該胺基的氫原子的全部或一部分也可以被碳數為1~6的烴基取代。而且,在著色組成物中所使用的[V]化合物的情況時,該胺基亦可被碳數為1~6的烷基取代。A為單鍵、羰基、羰氧基、羰基亞甲基、亞磺醯基、磺醯基、亞甲基或碳數為2~6的伸烷基。其中,上述亞甲基及伸烷基的氫原子的全部或一部分也可以被氰基、鹵素原子或氟烷基取代。 In the above formula (2), R 7 to R 16 each independently represent a hydrogen atom, an electron withdrawing group or an amine group. Among them, at least one of R 7 to R 16 is an amine group. Further, all or a part of the hydrogen atom of the amine group may be substituted with a hydrocarbon group having 1 to 6 carbon atoms. Further, in the case of the [V] compound used in the coloring composition, the amine group may be substituted with an alkyl group having 1 to 6 carbon atoms. A is a single bond, a carbonyl group, a carbonyloxy group, a carbonylmethylene group, a sulfinyl group, a sulfonyl group, a methylene group or an alkylene group having 2 to 6 carbon atoms. Here, all or a part of the hydrogen atom of the above methylene group and alkylene group may be substituted by a cyano group, a halogen atom or a fluoroalkyl group.
上述式(1)及式(2)中,R1~R16所表示的吸電子基例如可列舉鹵素原子、氰基、硝基、三氟甲基、羧基、醯基、烷基磺醯基、烷氧基磺醯基、二氰基乙烯基、三氰基乙烯基、磺醯基等。該些基中優選為硝基、烷氧基磺醯 基、三氟甲基。A所表示的基優選為磺醯基、亦可被氟烷基取代的亞甲基。 In the above formula (1) and formula (2), examples of the electron withdrawing group represented by R 1 to R 16 include a halogen atom, a cyano group, a nitro group, a trifluoromethyl group, a carboxyl group, a decyl group, and an alkylsulfonyl group. , alkoxysulfonyl, dicyanovinyl, tricyanovinyl, sulfonyl and the like. Preferred among these groups are a nitro group, an alkoxysulfonyl group, and a trifluoromethyl group. The group represented by A is preferably a sulfonyl group or a methylene group which may be substituted by a fluoroalkyl group.
作為上述式(1)及式(2)所表示的化合物,優選為2,2-雙(4-胺基苯基)六氟丙烷、2,3-雙(4-胺基苯基)丁二腈、4,4'-二胺基二苯甲酮、4,4'-二胺基苯甲酸苯酯、4,4'-二胺基二苯基碸、1,4-二胺基-2-氯苯、1,4-二胺基-2-溴苯、1,4-二胺基-2-碘苯、1,4-二胺基-2-硝基苯、1,4-二胺基-2-三氟甲基苯、2,5-二胺基苄腈、2,5-二胺基苯乙酮、2,5-二胺基苯甲酸、2,2'-二氯聯苯胺、2,2'-二溴聯苯胺、2,2'-二碘聯苯胺、2,2'-二硝基聯苯胺、2,2'-雙(三氟甲基)聯苯胺、3-胺基苯磺酸乙酯、3,5-雙三氟甲基-1,2-二胺基苯、4-胺基硝基苯、N,N-二甲基-4-硝基苯胺,更優選為4,4'-二胺基二苯基碸、2,2-雙(4-胺基苯基)六氟丙烷、2,2'-雙(三氟甲基)聯苯胺、3-胺基苯磺酸乙酯、3,5-雙三氟甲基-1,2-二胺基苯、4-胺基硝基苯、N,N-二甲基-4-硝基苯胺。 The compound represented by the above formula (1) and formula (2) is preferably 2,2-bis(4-aminophenyl)hexafluoropropane or 2,3-bis(4-aminophenyl)butane. Nitrile, 4,4'-diaminobenzophenone, phenyl 4,4'-diaminobenzoate, 4,4'-diaminodiphenylanthracene, 1,4-diamino-2 -Chlorobenzene, 1,4-diamino-2-bromobenzene, 1,4-diamino-2-iodobenzene, 1,4-diamino-2-nitrobenzene, 1,4-diamine Benzyl-2-trifluoromethylbenzene, 2,5-diaminobenzonitrile, 2,5-diaminoacetophenone, 2,5-diaminobenzoic acid, 2,2'-dichlorobenzidine , 2,2'-dibromobenzidine, 2,2'-diiodobenzidine, 2,2'-dinitrobenzidine, 2,2'-bis(trifluoromethyl)benzidine, 3-amine Ethyl benzenesulfonate, 3,5-bistrifluoromethyl-1,2-diaminobenzene, 4-aminonitrobenzene, N,N-dimethyl-4-nitroaniline, more preferably Is 4,4'-diaminodiphenylanthracene, 2,2-bis(4-aminophenyl)hexafluoropropane, 2,2'-bis(trifluoromethyl)benzidine, 3-amino group Ethyl benzenesulfonate, 3,5-bistrifluoromethyl-1,2-diaminobenzene, 4-aminonitrobenzene, N,N-dimethyl-4-nitroaniline.
上述式(1)及式(2)所表示的化合物可單獨使用或將2種以上混合使用。作為上述式(1)及式(2)所表示的化合物的含有比例,相對於[I]鹼溶性樹脂100質量份而言優選為0.1質量份~20質量份,更優選為0.2質量份~10質量份。通過使上述式(1)及式(2)所表示的化合物的含有比例為上述範圍,能夠以更高的水準而兼顧著色組成物的保存穩定性與低溫硬化。 The compounds represented by the above formulas (1) and (2) may be used singly or in combination of two or more. The content ratio of the compound represented by the above formula (1) and the formula (2) is preferably 0.1 parts by mass to 20 parts by mass, more preferably 0.2 parts by mass to 10 parts by mass per 100 parts by mass of the [I] alkali-soluble resin. Parts by mass. By setting the content ratio of the compound represented by the above formulas (1) and (2) to the above range, it is possible to achieve both the storage stability of the colored composition and the low-temperature curing at a higher level.
如果使反應性高的一般的伯胺化合物或仲胺化合物 與環氧化合物共存,則在組成物溶液的保存中,由於胺的對環氧基的親核進攻而進行硬化反應,從而存在有損作為製品的品質的可能。然而,在使用三級胺的情況下,由於反應性比較低、或者在組成部中與環氧化合物共存,保存穩定性變良好。 If a general primary or secondary amine compound having high reactivity is obtained In the case of coexistence with the epoxy compound, in the storage of the composition solution, the hardening reaction proceeds due to the nucleophilic attack of the epoxy group on the amine, which may impair the quality of the product. However, in the case of using a tertiary amine, storage stability is improved because the reactivity is relatively low or coexistence with the epoxy compound in the composition portion.
三級胺化合物可使用選自由下述式(5)所表示的化合物所構成的群組的至少1種。 As the tertiary amine compound, at least one selected from the group consisting of compounds represented by the following formula (5) can be used.
在上述式(5)中,R24~R26分別獨立為碳數為1~20的烷基、碳數為6~18的芳基或碳數為7~30的芳烷基。其中,R24及R25亦可相互鍵結,與該些所鍵結的氮原子一同形成環狀結構。上述烷基、芳基及芳烷基的氫原子的一部分或全部亦可被取代。 In the above formula (5), R 24 to R 26 are each independently an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 18 carbon atoms or an aralkyl group having 7 to 30 carbon atoms. Wherein R 24 and R 25 may be bonded to each other to form a cyclic structure together with the nitrogen atoms bonded thereto. Some or all of the hydrogen atoms of the above alkyl group, aryl group and aralkyl group may be substituted.
上述式(5)中,R24~R26所表示的上述碳數為1~20的烷基例如可列舉直鏈狀或分支狀的甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、月桂基、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、二十烷基等。 In the above formula (5), the alkyl group having 1 to 20 carbon atoms represented by R 24 to R 26 may, for example, be a linear or branched methyl group, an ethyl group, a propyl group, a butyl group or a pentyl group. Hexyl, heptyl, octyl, decyl, decyl, lauryl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecane Base, nonadecyl, eicosyl and the like.
上述式(5)中,R24~R26所表示的碳數為6~18的芳基例如可列舉苯基、萘基等。 In the above formula (5), examples of the aryl group having 6 to 18 carbon atoms represented by R 24 to R 26 include a phenyl group and a naphthyl group.
上述式(5)中,R24~R26所表示的碳數為7~30的芳烷基例如可列舉苄基、苯乙基等。 In the above formula (5), examples of the aralkyl group having 7 to 30 carbon atoms represented by R 24 to R 26 include a benzyl group and a phenethyl group.
三級胺化合物例如可列舉N,N-二甲基苄基胺、三苯基胺、三丁基胺、三辛基胺、三(十二烷基)胺、二丁基苄基胺、三萘基胺、N-乙基-N-甲基苯胺、N,N-二乙基苯胺、N-苯基-N-甲基苯胺、N,N-二甲基-對甲苯胺、N,N-二甲基-4-溴苯胺、N,N-二甲基-4-甲氧基苯胺、N-苯基呱啶、N-(4-甲氧基苯基)呱啶、N-苯基-1,2,3,4-四氫異喹啉、6-苄基氧基-N-苯基-7-甲氧基-1,2,3,4-四氫異喹啉、N,N'-二甲基呱嗪、N,N-二甲基環己基胺、2-二甲基胺基甲基苯酚、2,4,6-三(二甲基胺基甲基)苯酚等。 Examples of the tertiary amine compound include N,N-dimethylbenzylamine, triphenylamine, tributylamine, trioctylamine, tris(dodecyl)amine, dibutylbenzylamine, and trisole. Naphthylamine, N-ethyl-N-methylaniline, N,N-diethylaniline, N-phenyl-N-methylaniline, N,N-dimethyl-p-toluidine, N,N - dimethyl-4-bromoaniline, N,N-dimethyl-4-methoxyaniline, N-phenyl acridine, N-(4-methoxyphenyl)acridine, N-phenyl -1,2,3,4-tetrahydroisoquinoline, 6-benzyloxy-N-phenyl-7-methoxy-1,2,3,4-tetrahydroisoquinoline, N,N '-Dimethylpyridazine, N,N-dimethylcyclohexylamine, 2-dimethylaminomethylphenol, 2,4,6-tris(dimethylaminomethyl)phenol, and the like.
該些三級胺化合物中,優選三辛基胺、2-二甲基胺基甲基苯酚、N,N-二乙基苯胺等。三級胺化合物可單獨使用或將2種以上混合使用。 Among these tertiary amine compounds, trioctylamine, 2-dimethylaminomethylphenol, N,N-diethylaniline and the like are preferable. The tertiary amine compound may be used singly or in combination of two or more.
作為著色組成物中的三級胺化合物的含有比例,相對於[I]鹼溶性樹脂100質量份而言優選為0.1質量份~10質量份,更優選為0.5質量份~5質量份。通過使三級胺化合物的含有比例為上述特定範圍,能夠以更高的水準而兼顧著色組成物的保存穩定性與低溫硬化。 The content ratio of the tertiary amine compound in the coloring composition is preferably 0.1 parts by mass to 10 parts by mass, more preferably 0.5 parts by mass to 5 parts by mass, per 100 parts by mass of the [I] alkali-soluble resin. By setting the content ratio of the tertiary amine compound to the above specific range, it is possible to achieve both the storage stability of the colored composition and the low-temperature curing at a higher level.
胺鹽及鏻鹽可使用選自由下述式(6)所表示的化合物所構成的群組的至少1種。 As the amine salt and the phosphonium salt, at least one selected from the group consisting of compounds represented by the following formula (6) can be used.
[化18]
在上述式(6)中,A1為氮原子或磷原子。R27~R30分別獨立為氫原子、碳數為1~20的烷基、碳數為6~18的芳基或碳數為7~30的芳烷基。其中,該些基的氫原子的一部分或全部亦可被取代。Q-為1價陰離子。 In the above formula (6), A 1 is a nitrogen atom or a phosphorus atom. R 27 to R 30 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 18 carbon atoms or an aralkyl group having 7 to 30 carbon atoms. Among them, some or all of the hydrogen atoms of the groups may be substituted. Q - is a monovalent anion.
上述式(6)中,R27~R30所表示的碳數為1~20的烷基例如可列舉直鏈狀或分支狀的甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、月桂基、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、二十烷基等。 In the above formula (6), the alkyl group having 1 to 20 carbon atoms represented by R 27 to R 30 may, for example, be a linear or branched methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group or a hexyl group. , heptyl, octyl, decyl, decyl, lauryl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl , nonadecyl, eicosyl and the like.
上述R27~R30所表示的碳數為6~18的芳基例如可列舉苯基、萘基等。 Examples of the aryl group having 6 to 18 carbon atoms represented by the above R 27 to R 30 include a phenyl group and a naphthyl group.
上述式(6)中,R27~R30所表示的碳數為7~30的芳烷基例如可列舉苄基、苯乙基等。 In the above formula (6), examples of the aralkyl group having 7 to 30 carbon atoms represented by R 27 to R 30 include a benzyl group and a phenethyl group.
上述式(6)中,Q-所表示的1價陰離子例如可列舉氯化物離子、溴化物離子、碘化物離子、氰化物離子、硝酸根離子、亞硝酸根離子、次氯酸根離子、亞氯酸根離子、氯酸根離子、過氯酸根離子、高錳酸根離子、碳酸氫根離子、磷酸二氫根離子、硫化氫根離子、硫氰酸根離子、羧酸離子、磺酸離子、苯氧基離子、四氟硼酸鹽離子、四芳基硼酸鹽離子、六氟銻酸鹽離子等。 In the above formula (6), the monovalent anion represented by Q - may, for example, be a chloride ion, a bromide ion, an iodide ion, a cyanide ion, a nitrate ion, a nitrite ion, a hypochlorite ion, or a chlorous acid. Acid ion, chlorate ion, perchlorate ion, permanganate ion, hydrogencarbonate ion, dihydrogen phosphate ion, hydrogen sulfide ion, thiocyanate ion, carboxylate ion, sulfonate ion, phenoxy ion , tetrafluoroborate ion, tetraaryl borate ion, hexafluoroantimonate ion, and the like.
當A1為氮原子的情況時,亦即銨鹽例如可列舉四甲基氯化銨、四丁基氯化銨、十二烷基二甲基苄基氯化銨、辛基三甲基氯化銨、癸基三甲基氯化銨、十二烷基三甲基氯化銨、十四烷基三甲基氯化銨、鯨蠟基三甲基氯化銨、硬脂基三甲基氯化銨、十六烷基三甲基溴化銨、苄基三甲基氯化銨、苄基三乙基氯化銨、苯紮氯銨、苯紮溴銨、二癸基二甲基氯化銨、二硬脂基二甲基氯化銨。 When A 1 is a nitrogen atom, that is, the ammonium salt may, for example, be tetramethylammonium chloride, tetrabutylammonium chloride, dodecyldimethylbenzylammonium chloride or octyltrimethyl chloride. Ammonium, mercaptotrimethylammonium chloride, dodecyltrimethylammonium chloride, tetradecyltrimethylammonium chloride, cetyltrimethylammonium chloride, stearyltrimethyl Ammonium chloride, cetyltrimethylammonium bromide, benzyltrimethylammonium chloride, benzyltriethylammonium chloride, benzalkonium chloride, benzalkonium bromide, dimercaptodimethyl chloride Ammonium, distearyl dimethyl ammonium chloride.
當A1為磷原子的情況時,亦即鏻鹽例如可列舉四苯基鏻.四苯基硼酸鹽、四苯基鏻.四(對甲苯基)硼酸鹽、四苯基鏻.四(對乙基苯基)硼酸鹽、四苯基鏻.四(對甲氧基苯基)硼酸鹽、四苯基鏻.四(對乙氧基苯基)硼酸鹽、四苯基鏻.四(對第三丁氧基苯基)硼酸鹽、四苯基鏻.四(間甲苯基)硼酸鹽、四苯基鏻.四(間甲氧基苯基)硼酸鹽、三(對甲苯基)苯基鏻.四(對甲苯基)硼酸鹽、四(對甲苯基)鏻.四(對甲苯基)硼酸鹽、三(對甲氧基苯基)苯基鏻.四(對甲苯基)硼酸鹽、四苯基鏻硫氰酸鹽、丁基三苯基鏻硫氰酸鹽、甲基三苯基鏻硫氰酸鹽、對甲苯基三苯基鏻硫氰酸鹽等。 When A 1 is a phosphorus atom, that is, a phosphonium salt is exemplified by tetraphenylphosphonium. Tetraphenylborate, tetraphenylphosphonium. Tetrakis(p-tolyl)borate, tetraphenylphosphonium. Tetrakis(p-ethylphenyl)borate, tetraphenylphosphonium. Tetrakis(p-methoxyphenyl)borate, tetraphenylphosphonium. Tetrakis(p-ethoxyphenyl)borate, tetraphenylphosphonium. Tetrakis(p-tert-butoxyphenyl)borate, tetraphenylphosphonium. Tetra(m-tolyl)borate, tetraphenylphosphonium. Tetra(m-methoxyphenyl)borate, tris(p-tolyl)phenylhydrazine. Tetrakis(p-tolyl)borate, tetra (p-tolyl) oxime. Tetrakis(p-tolyl)borate, tris(p-methoxyphenyl)phenylhydrazine. Tetra(p-tolyl)borate, tetraphenylphosphonium thiocyanate, butyltriphenylphosphonium thiocyanate, methyltriphenylphosphonium thiocyanate, p-tolyltriphenylsulfonium thiocyanate Salt and so on.
該些胺鹽及鏻鹽中優選四甲基氯化銨、丁基三苯基鏻硫氰酸鹽。胺鹽及鏻鹽可單獨使用或將2種以上混合使用。 Among these amine salts and phosphonium salts, tetramethylammonium chloride and butyltriphenylphosphonium thiocyanate are preferred. The amine salt and the phosphonium salt may be used singly or in combination of two or more.
作為著色組成物中的胺鹽及鏻鹽的含有比例,相對於[I]鹼溶性樹脂100質量份而言優選為0.05質量份~10質量份,更優選為0.1質量份~5質量份。通過使胺鹽及鏻鹽的含有比例為上述特定範圍,能夠以更高的水準而兼顧 著色組成物的保存穩定性與低溫硬化。 The content ratio of the amine salt and the cerium salt in the coloring composition is preferably 0.05 parts by mass to 10 parts by mass, more preferably 0.1 parts by mass to 5 parts by mass, per 100 parts by mass of the [I] alkali-soluble resin. By setting the content ratio of the amine salt and the onium salt to the above specific range, it is possible to achieve a higher level The storage stability of the colored composition is low temperature hardening.
脒鹽可使用選自由下述式(7)所表示的化合物的鹽所構成的群組的至少1種。 As the onium salt, at least one selected from the group consisting of salts of the compounds represented by the following formula (7) can be used.
在上述式(7)中,m是2~6的整數。其中,伸烷基所具有的氫原子的一部分或全部亦可被有機基取代。另外,上述伸烷基是指四氫嘧啶環中的伸烷基及在式(7)中以(CH2)m而表示的伸烷基這兩者。 In the above formula (7), m is an integer of 2-6. Among them, a part or all of the hydrogen atoms of the alkylene group may be substituted by an organic group. Further, the above alkylene group means both an alkylene group in the tetrahydropyrimidine ring and an alkylene group represented by (CH 2 ) m in the formula (7).
上述伸烷基所亦可具有的作為取代基的有機基例如可列舉:甲基、乙基、異丙基、正丁基、第三丁基、正己基等碳數為1~6的烷基;羥基甲基、2-羥基乙基、1-羥基丙基、2-羥基丙基、3-羥基丙基、2-羥基異丙基、3-羥基-第三丁基、6-羥基己基等碳數為1~6的羥基烷基;二甲基胺基、甲基乙基胺基、二乙基胺基、二異丙基 胺基、二丁基胺基、第三丁基甲基胺基、二正己基胺基等碳數為2~12的二烷基胺基等。 Examples of the organic group which may be a substituent of the alkylene group include a methyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a t-butyl group and a n-hexyl group. ; hydroxymethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxyisopropyl, 3-hydroxy-tert-butyl, 6-hydroxyhexyl, etc. a hydroxyalkyl group having 1 to 6 carbon atoms; dimethylamino group, methyl ethylamino group, diethylamino group, diisopropyl group A dialkylamino group having 2 to 12 carbon atoms such as an amine group, a dibutylamino group, a tert-butylmethylamino group or a di-n-hexylamino group.
上述式(7)所表示的化合物可列舉1,5-二氮雜雙環[4,3,0]-壬烯-5(DBN)、1,5-二氮雜雙環[4,4,0]-癸烯-5、1,8-二氮雜雙環[5,4,0]-十一碳烯-7(DBU)、5-羥基丙基-1,8-二氮雜雙環[5,4,0]-十一碳烯-7、5-二丁基胺基-1,8-二氮雜雙環[5,4,0]-十一碳烯-7等。該些化合物中優選DBN及DBU。 Examples of the compound represented by the above formula (7) include 1,5-diazabicyclo[4,3,0]-nonene-5 (DBN) and 1,5-diazabicyclo[4,4,0]. -decene-5,1,8-diazabicyclo[5,4,0]-undecene-7 (DBU), 5-hydroxypropyl-1,8-diazabicyclo[5,4 , 0]-undecene-7,5-dibutylamino-1,8-diazabicyclo[5,4,0]-undecene-7 and the like. Among these compounds, DBN and DBU are preferred.
上述式(7)所表示的化合物用以形成鹽的酸可列舉有機酸及無機酸。 Examples of the acid represented by the above formula (7) for forming a salt include an organic acid and an inorganic acid.
有機酸例如可列舉羧酸、單烷基碳酸、芳香族羥基化合物、磺酸等。 Examples of the organic acid include a carboxylic acid, a monoalkyl carbonate, an aromatic hydroxy compound, and a sulfonic acid.
該些酸中優選羧酸、芳香族羥基化合物、磺酸,更優選飽和脂肪酸、芳香族羥基化合物、磺酸,特別優選作為強酸的磺酸,最優選甲苯磺酸、甲磺酸、辛基苯磺酸。脒鹽優選為DBU與甲苯磺酸的鹽、DBU與辛基苯磺酸的鹽、DBN與甲苯磺酸的鹽、DBN與辛基苯磺酸的鹽。 Among these acids, a carboxylic acid, an aromatic hydroxy compound, a sulfonic acid is preferred, a saturated fatty acid, an aromatic hydroxy compound, a sulfonic acid is more preferred, a sulfonic acid as a strong acid is particularly preferred, and toluenesulfonic acid, methanesulfonic acid, and octylbenzene are most preferred. Sulfonic acid. The onium salt is preferably a salt of DBU with toluenesulfonic acid, a salt of DBU with octylbenzenesulfonic acid, a salt of DBN with toluenesulfonic acid, or a salt of DBN with octylbenzenesulfonic acid.
脒鹽可單獨使用或者將2種以上混合使用。作為著色組成物中的脒鹽的含有比例,相對於[I]鹼溶性樹脂100質量份而言優選為0.1質量份~10質量份,更優選為0.5質量份~5質量份。通過使脒鹽的含有比例為上述特定範圍,能夠以更高的水準而兼顧著色組成物的保存穩定性與低溫硬化。 The onium salts may be used singly or in combination of two or more. The content ratio of the cerium salt in the coloring composition is preferably 0.1 parts by mass to 10 parts by mass, more preferably 0.5 parts by mass to 5 parts by mass, per 100 parts by mass of the [I] alkali-soluble resin. By setting the content ratio of the onium salt to the above specific range, it is possible to achieve both the storage stability of the colored composition and the low-temperature curing at a higher level.
醯胺化合物可使用選自由具有下述式(8)~式(10)所表示的醯胺基的化合物所構成的群組的至少1種。 As the guanamine compound, at least one selected from the group consisting of compounds having a guanamine group represented by the following formulas (8) to (10) can be used.
在上述式(8)中,R31及R32分別獨立為氫原子、碳數為1~12的烷基、環己基、苯基、萘基、乙烯基、或2- 吡啶基。其中,上述碳數為1~12的烷基、苯基及萘基亦可被碳數為1~6的烷基、鹵素原子、羥基、羧基或乙醯基取代。 In the above formula (8), R 31 and R 32 each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cyclohexyl group, a phenyl group, a naphthyl group, a vinyl group or a 2-pyridyl group. Here, the alkyl group having 1 to 12 carbon atoms, a phenyl group and a naphthyl group may be substituted by an alkyl group having 1 to 6 carbon atoms, a halogen atom, a hydroxyl group, a carboxyl group or an ethyl fluorenyl group.
在上述式(9)中,R33及R34分別獨立為氫原子、碳數為1~12的烷基或環己基。A2為亞甲基、碳數為2~12的伸烷基、伸苯基、萘撐、或乙烯撐。其中,上述亞甲基、碳數為2~12的伸烷基、伸苯基及萘撐亦可被碳數為1~6的烷基、鹵素原子取代。 In the above formula (9), R 33 and R 34 each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or a cyclohexyl group. A 2 is a methylene group, an alkylene group having a carbon number of 2 to 12, a phenylene group, a naphthene, or an ethylene support. The methylene group, the alkylene group having 2 to 12 carbon atoms, the phenylene group and the naphthene group may be substituted by an alkyl group having 1 to 6 carbon atoms or a halogen atom.
在上述式(10)中,R35及R36分別獨立為氫原子、碳數為1~12的烷基或環己基。A3為亞甲基、碳數為2~12的伸烷基、伸苯基、萘撐、或乙烯撐。其中,上述亞甲基、碳數為2~12的伸烷基、伸苯基及萘撐亦可被碳數為1~6的烷基、鹵素原子取代。 In the above formula (10), R 35 and R 36 each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or a cyclohexyl group. A 3 is a methylene group, an alkylene group having a carbon number of 2 to 12, a phenylene group, a naphthene, or an ethylene support. The methylene group, the alkylene group having 2 to 12 carbon atoms, the phenylene group and the naphthene group may be substituted by an alkyl group having 1 to 6 carbon atoms or a halogen atom.
上述式(8)所表示的醯胺化合物是在分子內具有一個醯胺鍵的化合物。其具體例例如可列舉乙醯胺、N-甲基乙醯胺、N-乙基乙醯胺、鄰胺甲醯苯甲酸、丙烯醯胺、苯甲醯胺、萘甲醯胺、煙醯胺、異煙醯胺等。 The guanamine compound represented by the above formula (8) is a compound having one guanamine bond in the molecule. Specific examples thereof include acetamide, N-methylacetamide, N-ethylacetamide, o-amine methyl benzoic acid, acrylamide, benzamide, naphthylamine, and nicotinamide. , isoniazid, etc.
自可使在室溫下的保存穩定性、所得的著色圖案等的耐熱性、電壓保持率等提高的觀點考慮,該些化合物中優選乙醯胺、N-甲基乙醯胺、鄰胺甲醯苯甲酸。 Among these compounds, acetamide, N-methylacetamide, and orthoamine A are preferable from the viewpoints of improvement in storage stability at room temperature, heat resistance of the obtained coloring pattern, and the like. Benzoic acid.
上述式(9)及式(10)所表示的化合物是在分子內具有2個醯胺鍵的化合物。其具體例例如可列舉鄰苯二甲醯胺、間苯二甲醯胺、對苯二甲醯胺、丙二醯胺、琥珀醯胺、N,N'-二乙醯基-對苯二胺、N,N'-二乙醯基-己二胺、N,N'- 二乙醯基-十二烷基亞甲基二胺等。 The compound represented by the above formula (9) and formula (10) is a compound having two indoleamine bonds in the molecule. Specific examples thereof include o-xylyleneamine, m-xylyleneamine, p-xylyleneamine, malonamide, succinimide, N,N'-diethylindenyl-p-phenylenediamine. , N,N'-diethylene-hexamethylenediamine, N,N'- Diethyl decyl-dodecylmethylenediamine and the like.
自能夠以高的水準兼顧保存穩定性與低溫硬化的觀點考慮,該些化合物中優選間苯二甲醯胺、己二醯胺、N,N'-二乙醯基-對苯二胺、N,N'-二乙醯基-己二胺。 Among these compounds, m-xylyleneamine, hexamethylenediamine, N,N'-diethylhydrazine-p-phenylenediamine, N are preferable from the viewpoint of achieving high stability in both storage stability and low-temperature hardening. , N'-diethenyl-hexanediamine.
醯胺化合物可單獨使用或者將2種以上混合使用。作為著色組成物中的醯胺化合物的含有比例,相對於[I]鹼溶性樹脂100質量份而言優選為0.1質量份~10質量份,更優選為0.5質量份~5質量份。通過使醯胺化合物的含有比例為上述特定範圍,能夠以更高的水準兼顧著色組成物的保存穩定性與低溫硬化。 The guanamine compound may be used singly or in combination of two or more. The content ratio of the guanamine compound in the coloring composition is preferably 0.1 parts by mass to 10 parts by mass, more preferably 0.5 parts by mass to 5 parts by mass, per 100 parts by mass of the [I] alkali-soluble resin. By setting the content ratio of the guanamine compound to the above specific range, it is possible to achieve both the storage stability of the colored composition and the low-temperature curing at a higher level.
硫醇化合物是在1分子中具有2個以上巰基的化合物。硫醇化合物只要在1分子中具有2個以上巰基就並無特別限定,可使用選自由下述式(11)所表示的化合物所構成的群組的至少1種。 The thiol compound is a compound having two or more mercapto groups in one molecule. The thiol compound is not particularly limited as long as it has two or more thiol groups in one molecule, and at least one selected from the group consisting of compounds represented by the following formula (11) can be used.
在式(11)中,R37為亞甲基、碳數為2~10的伸烷基。其中,該些基的氫原子的一部分或全部也可以被烷基取代。Y1為單鍵、-CO-或O-CO-*。其中,附有*的鍵與R37鍵結。n為2~10的整數。A4為亦可具有1個或多個醚鍵的碳數為2~70的n價烴基,或者在n為3的情況時為 下述式(12)所表示的基。 In the formula (11), R 37 is a methylene group and an alkylene group having 2 to 10 carbon atoms. Among them, some or all of the hydrogen atoms of the groups may be substituted with an alkyl group. Y 1 is a single bond, -CO-, or O-CO- *. Among them, the key with * is connected with the R 37 key. n is an integer from 2 to 10. A 4 is an n-valent hydrocarbon group having 2 to 70 carbon atoms which may have one or more ether linkages, or a group represented by the following formula (12) when n is 3.
在上述式(12)中,R38~R40分別獨立為亞甲基或碳數為2~6的伸烷基。“*”分別表示化學鍵。 In the above formula (12), R 38 to R 40 are each independently a methylene group or an alkylene group having 2 to 6 carbon atoms. " * " indicates a chemical bond, respectively.
作為上述式(11)所表示的化合物,典型的是可使用巰基羧酸與多元醇的酯化物等。構成酯化物的巰基羧酸例如可列舉巰基乙酸、3-巰基丙酸、3-巰基丁酸、3-巰基戊酸等。而且,構成酯化物的多元醇例如可列舉乙二醇、丙二醇、三羥甲基丙烷、季戊四醇、四乙二醇、二季戊四醇、1,4-丁二醇、季戊四醇等。 As the compound represented by the above formula (11), an esterified product of a mercaptocarboxylic acid and a polyhydric alcohol can be typically used. Examples of the mercaptocarboxylic acid constituting the ester compound include mercaptoacetic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, 3-mercaptovaleric acid, and the like. Further, examples of the polyhydric alcohol constituting the ester compound include ethylene glycol, propylene glycol, trimethylolpropane, pentaerythritol, tetraethylene glycol, dipentaerythritol, 1,4-butanediol, and pentaerythritol.
上述式(11)所表示的化合物優選為三羥甲基丙烷三(3-巰基丙酸)酯、季戊四醇四(3-巰基丙酸)酯、四乙二醇雙(3-巰基丙酸)酯、二季戊四醇六(3-巰基丙酸)酯、季戊四醇四(巰基乙酸)酯、1,4-雙(3-巰基丁醯氧基)丁烷、季戊四醇四(3-巰基丁酸)酯、季戊四醇四(3-巰基戊酸)酯、1,3,5-三(3-巰基丁氧基乙基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮。 The compound represented by the above formula (11) is preferably trimethylolpropane tris(3-mercaptopropionic acid) ester, pentaerythritol tetrakis(3-mercaptopropionic acid) ester, tetraethylene glycol bis(3-mercaptopropionate) ester. Dipentaerythritol hexa(3-mercaptopropionic acid) ester, pentaerythritol tetrakis(mercaptoacetic acid) ester, 1,4-bis(3-mercaptobutyloxy)butane, pentaerythritol tetrakis(3-mercaptobutyrate), pentaerythritol Tetrakis(3-mercaptovalerate), 1,3,5-tris(3-mercaptobutoxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)- Triketone.
硫醇化合物的在1分子中具有2個以上巰基的化合物亦可使用下述式(13)~式(15)所表示的化合物。 As the compound having two or more mercapto groups in one molecule of the thiol compound, a compound represented by the following formulas (13) to (15) can also be used.
在上述式(13)中,R41為亞甲基或碳數為2~20的伸烷基。R42為亞甲基或碳數為2~6的直鏈或分支伸烷基。k為1~20的整數。 In the above formula (13), R 41 is a methylene group or an alkylene group having 2 to 20 carbon atoms. R 42 is a methylene group or a linear or branched alkyl group having 2 to 6 carbon atoms. k is an integer from 1 to 20.
在上述式(14)中,R43~R46分別獨立為氫原子、羥基或下述式(15)所表示的基。其中,R43~R46的至少1個是下述式(15)所表示的基。 In the above formula (14), R 43 to R 46 each independently represent a hydrogen atom, a hydroxyl group or a group represented by the following formula (15). However, at least one of R 43 to R 46 is a group represented by the following formula (15).
在上述式(15)中,R47為亞甲基或碳數為2~6的直 鏈或分支伸烷基。 In the above formula (15), R 47 is a methylene group or a linear or branched alkyl group having 2 to 6 carbon atoms.
硫醇化合物可單獨使用或者將2種以上混合使用。作為著色組成物中的硫醇化合物的含有比例,相對於[I]鹼溶性樹脂100質量份而言優選為1質量份~20質量份,更優選為5質量份~15質量份。通過使硫醇化合物的含有比例為上述特定範圍,能夠以更高的水準而兼顧著色組成物的保存穩定性與低溫硬化。 The thiol compound may be used singly or in combination of two or more. The content ratio of the thiol compound in the coloring composition is preferably 1 part by mass to 20 parts by mass, more preferably 5 parts by mass to 15 parts by mass, per 100 parts by mass of the [I] alkali-soluble resin. By setting the content ratio of the thiol compound to the above specific range, it is possible to achieve both the storage stability of the colored composition and the low-temperature curing at a higher level.
嵌段聚異氰酸酯化合物是使異氰酸酯基與含有活性氫基的化合物(阻斷劑)反應而在常溫成為惰性的化合物,具有如下的性質:若對其進行加熱,則阻斷劑解離而再生出異氰酸酯基。著色組成物含有嵌段聚異氰酸酯,以作為有效的交聯劑而進行異氰酸酯-羥基交聯反應,從而能夠以高的水準而兼顧著色組成物的保存穩定性與低溫硬化。 The block polyisocyanate compound is a compound which reacts with an active hydrogen group-containing compound (blocking agent) and is inert at normal temperature, and has a property that if it is heated, the blocking agent dissociates and regenerates the isocyanate. base. The colored composition contains a block polyisocyanate, and the isocyanate-hydroxyl crosslinking reaction is carried out as an effective crosslinking agent, so that the storage stability and the low-temperature curing of the colored composition can be achieved at a high level.
嵌段聚異氰酸酯化合物可通過由脂肪族或脂環族二異氰酸酯而衍生的聚異氰酸酯與具有活性氫的化合物(阻斷劑)的公知的反應而獲得。 The blocked polyisocyanate compound can be obtained by a known reaction of a polyisocyanate derived from an aliphatic or alicyclic diisocyanate with a compound (blocker) having an active hydrogen.
二異氰酸酯例如可列舉四亞甲基二異氰酸酯、戊烷二異氰酸酯、六亞甲基二異氰酸酯(HDI)、2,2,4-三甲基-1,6-二異氰酸基己烷、2,4,4-三甲基-1,6-二異氰酸基己烷、賴胺酸二異氰酸酯、異佛爾酮二異氰酸酯(IPDI)、1,3-雙(異氰酸酯基甲基)環己烷、4,4-二環己基甲烷二異氰酸酯、降冰片烯二異氰酸酯、亞甲苯二異氰酸酯、4,4'-二苯基甲烷二異氰酸酯、1,5-萘二異氰酸酯、聯甲苯胺二異氰酸酯、 二甲苯胺異氰酸酯、1,4-四亞甲基二異氰酸酯、1,5-五亞甲基二異氰酸酯、1,6-六亞甲基二異氰酸酯、3-異氰酸酯甲基-3,5,5-三甲基環己基二異氰酸酯等。 Examples of the diisocyanate include tetramethylene diisocyanate, pentane diisocyanate, hexamethylene diisocyanate (HDI), 2,2,4-trimethyl-1,6-diisocyanatohexane, and 2 , 4,4-trimethyl-1,6-diisocyanatohexane, lysine diisocyanate, isophorone diisocyanate (IPDI), 1,3-bis(isocyanatemethyl)cyclohexane Alkane, 4,4-dicyclohexylmethane diisocyanate, norbornene diisocyanate, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 1,5-naphthalene diisocyanate, tolidine diisocyanate, Xylidine isocyanate, 1,4-tetramethylene diisocyanate, 1,5-pentamethylene diisocyanate, 1,6-hexamethylene diisocyanate, 3-isocyanate methyl-3,5,5- Trimethylcyclohexyl diisocyanate or the like.
作為市售品,例如:用丁酮的肟對異氰酸酯基進行嵌段而成者可列舉Duranate(注冊商標)TPA-B80E、TPA-B80X、E402-B80T、MF-B60XN、MF-B60X、MF-B80M(以上由旭化成工業公司製造);用活性亞甲基對異氰酸酯基進行嵌段而成者可列舉Duranate(注冊商標)MF-K60X(旭化成工業公司);具有(甲基)丙烯醯基的異氰酸酯化合物的嵌段體可列舉Karenz(注冊商標)MOI-BP、Karenz(注冊商標)MOI-BM(以上由昭和電工公司製造)。該些市售品中,在使用Duranate(注冊商標)E402-B80T、MF-K60X的情況時表現出高的柔韌性,通過製成與其他化合物的混合類而使用,可自由地控制其硬度,因此優選使用。 As a commercial item, for example, Duranate (registered trademark) TPA-B80E, TPA-B80X, E402-B80T, MF-B60XN, MF-B60X, MF- can be cited by blocking the isocyanate group with hydrazine of methyl ethyl ketone. B80M (the above is manufactured by Asahi Kasei Industrial Co., Ltd.); those which are blocked by an active methylene group to beocyanate groups include Duranate (registered trademark) MF-K60X (Asahi Kasei Kogyo Co., Ltd.); isocyanate having a (meth) acrylonitrile group. Examples of the block of the compound include Karenz (registered trademark) MOI-BP and Karenz (registered trademark) MOI-BM (all manufactured by Showa Denko Co., Ltd.). Among these commercial products, when using Duranat (registered trademark) E402-B80T or MF-K60X, high flexibility is exhibited, and by using a mixture with other compounds, the hardness can be freely controlled. It is therefore preferably used.
由二異氰酸酯而衍生的聚異氰酸酯例如可列舉異三聚氰酸酯型聚異氰酸酯、縮二脲型聚異氰酸酯、胺基甲酸酯型聚異氰酸酯、脲基甲酸酯型聚異氰酸酯等。自硬化性的觀點考慮,優選異三聚氰酸酯型聚異氰酸酯。 Examples of the polyisocyanate derived from the diisocyanate include a hetero-cyanate type polyisocyanate, a biuret type polyisocyanate, a urethane type polyisocyanate, and an allophanate type polyisocyanate. From the viewpoint of hardenability, a isocyanurate type polyisocyanate is preferred.
阻斷劑例如可列舉醇類化合物、酚類化合物、活性亞甲基類化合物、硫醇類化合物、醯胺類化合物、醯亞胺類化合物、咪唑類化合物、吡唑類化合物、脲類化合物、肟類化合物、胺類化合物、亞胺類化合物、吡啶類化合物等。 Examples of the blocking agent include an alcohol compound, a phenol compound, an active methylene compound, a thiol compound, a guanamine compound, a quinone compound, an imidazole compound, a pyrazole compound, a urea compound, and the like. An anthracene compound, an amine compound, an imine compound, a pyridine compound or the like.
醇類化合物例如可列舉甲醇、乙醇、丙醇、丁醇、2-乙基己醇、甲基溶纖劑、丁基溶纖劑、甲基卡必醇、苯甲醇、環己醇等;酚類化合物例如可列舉苯酚、甲酚、乙基苯酚、丁基苯酚、壬基苯酚、二壬基苯酚、苯乙烯化苯酚、羥基苯甲酸酯等;活性亞甲基類化合物例如可列舉丙二酸二甲酯、丙二酸二乙酯、乙醯乙酸甲酯、乙醯乙酸乙酯、乙醯丙酮等;硫醇類化合物例如可列舉丁基硫醇、十二烷基硫醇等;醯胺類化合物例如可列舉乙醯苯胺、乙醯胺、ε-己內醯胺、δ-戊內醯胺、γ-丁內醯胺等;醯亞胺類化合物例如可列舉琥珀醯亞胺、馬來醯亞胺等;咪唑類化合物例如可列舉咪唑、2-甲基咪唑等;吡唑類化合物例如可列舉3-甲基吡唑、3,5-二甲基吡唑、3,5-乙基吡唑等;脲類化合物例如可列舉尿素、硫脲、乙撐脲等;肟類化合物例如可列舉甲醛肟、乙醛肟、丙酮肟、丁酮肟、環己酮肟等;胺類化合物例如可列舉二苯基胺、苯胺、哢唑等;亞胺類化合物例如可列舉乙撐亞胺、聚乙烯亞胺等;吡啶類化合物例如可列舉2-羥基吡啶、2-羥基喹啉等。 Examples of the alcohol compound include methanol, ethanol, propanol, butanol, 2-ethylhexanol, methyl cellosolve, butyl cellosolve, methyl carbitol, benzyl alcohol, cyclohexanol, and the like; phenolic compounds; Examples thereof include phenol, cresol, ethylphenol, butylphenol, nonylphenol, dinonylphenol, styrenated phenol, and hydroxybenzoic acid ester; and examples of the active methylene-based compound include malonic acid Methyl ester, diethyl malonate, ethyl acetonitrile acetate, ethyl acetate, ethyl acetate, etc.; examples of the mercaptan compound include butyl mercaptan, dodecyl mercaptan, etc.; Examples of the compound include acetanilide, acetamide, ε-caprolactam, δ-valeroinamide, γ-butylidene, and the like; and the quinone imine compound may, for example, be a succinimide or malazone. Examples of the imidazole compound include imidazole and 2-methylimidazole; and pyrazole compounds include, for example, 3-methylpyrazole, 3,5-dimethylpyrazole, and 3,5-ethylpyrazole. Examples of the urea compound include urea, thiourea, and ethylene urea; and examples of the oxime compound include formaldehyde oxime and acetaldehyde oxime. Examples of the amine compound include diphenylamine, aniline, and carbazole; and the imine compound includes, for example, ethyleneimine or polyethyleneimine; and pyridine. Examples of the compound include 2-hydroxypyridine and 2-hydroxyquinoline.
嵌段聚異氰酸酯化合物可單獨使用或者將2種以上混 合使用。作為著色組成物中的嵌段聚異氰酸酯化合物的含有比例,相對於[I]鹼溶性樹脂100質量份而言優選為0.1質量份~10質量份,更優選為0.5質量份~5質量份。通過使嵌段聚異氰酸酯化合物的含有比例為上述範圍,能夠以更高的水準而兼顧著色組成物的保存穩定性與低溫硬化。 The block polyisocyanate compounds may be used singly or in combination of two or more kinds. Used together. The content ratio of the block polyisocyanate compound in the coloring composition is preferably 0.1 parts by mass to 10 parts by mass, more preferably 0.5 parts by mass to 5 parts by mass, per 100 parts by mass of the [I] alkali-soluble resin. When the content ratio of the block polyisocyanate compound is in the above range, it is possible to achieve both the storage stability of the colored composition and the low-temperature curing at a higher level.
含有咪唑環的化合物可使用選自由下述式(16)所表示的化合物所構成的群組的至少1種。 As the compound containing an imidazole ring, at least one selected from the group consisting of compounds represented by the following formula (16) can be used.
在上述式(16)中,A5、A6、A7及R48分別獨立為氫原子或亦可具有取代基的碳數為1~20的直鏈狀、分支狀或環狀的烴基。而且,A6與A7亦可相互連結而形成環。 In the above formula (16), each of A 5 , A 6 , A 7 and R 48 is independently a hydrogen atom or a linear, branched or cyclic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. Further, A 6 and A 7 may be bonded to each other to form a ring.
上述式(16)的A5、A6、A7及R48所表示的碳數為1~20的直鏈狀、分支狀或環狀的烴基例如可列舉:甲基、乙基、正丙基、異丙基、正丁基、異丁基、仲丁基、第三丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、 正十四烷基、正十五烷基、正十六烷基、正十七烷基、正十八烷基、正十九烷基、正二十烷基等碳數為1~20的烷基;環戊基、環丁基、環己基等碳數為3~20的環烷基;苯基、甲苯甲醯基、苄基、甲基苄基、二甲苯基、均三甲苯基、萘基、蒽基等碳數為6~20的芳基;降冰片基、三環癸基、四環十二烷基、金剛烷基、甲基金剛烷基、乙基金剛烷基、丁基金剛烷基等碳數為6~20的交聯脂環式烴基等。 Examples of the linear, branched or cyclic hydrocarbon group having 1 to 20 carbon atoms represented by A 5 , A 6 , A 7 and R 48 in the above formula (16) include methyl group, ethyl group and n-propyl group. Base, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-decyl, n-undecane Base, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, An alkyl group having a carbon number of 1 to 20 such as n-icosyl group; a cycloalkyl group having a carbon number of 3 to 20 such as a cyclopentyl group, a cyclobutyl group or a cyclohexyl group; a phenyl group, a tolylmethyl group, a benzyl group, and a methyl group; An aryl group having a carbon number of 6 to 20, such as a benzyl group, a xylyl group, a mesityl group, a naphthyl group or a fluorenyl group; a norbornyl group, a tricyclic fluorenyl group, a tetracyclododecyl group, an adamantyl group, a group A crosslinked alicyclic hydrocarbon group having a carbon number of 6 to 20, such as a hydroxyalkyl group, an ethyladamantyl group or a butyl hydroxyalkylene group.
上述烴基亦可被取代,該取代基的具體例可列舉:羥基;羧基;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-羥基丁基、2-羥基丁基、3-羥基丁基、4-羥基丁基等碳數為1~4的羥基烷基;甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、2-甲基丙氧基、1-甲基丙氧基、第三丁氧基等碳數為1~4的烷氧基;氰基;氰基甲基、2-氰基乙基、3-氰基丙基、4-氰基丁基等碳數為2~5的氰基烷基;甲氧基羰基、乙氧基羰基、第三丁氧基羰基等碳數為2~5的烷氧基羰基;甲氧基羰基甲氧基、乙氧基羰基甲氧基、第三丁氧基 羰基甲氧基等碳數為3~6的烷氧基羰基烷氧基;氟、氯等鹵素原子;氟甲基、三氟甲基、五氟乙基等氟烷基等。 The above hydrocarbon group may also be substituted, and specific examples of the substituent include a hydroxyl group; a carboxyl group; a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, and 3- Hydroxypropyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, etc. hydroxyalkyl group having a carbon number of 1 to 4; methoxy, ethoxy, n-propoxy Alkoxy group having a carbon number of 1 to 4, such as a group, an isopropoxy group, a n-butoxy group, a 2-methylpropoxy group, a 1-methylpropoxy group, a third butoxy group; a cyano group; a cyano group; a cyano group having a carbon number of 2 to 5 such as a methyl group, a 2-cyanoethyl group, a 3-cyanopropyl group or a 4-cyanobutyl group; a methoxycarbonyl group, an ethoxycarbonyl group, and a third butoxy group Alkoxycarbonyl group having a carbon number of 2 to 5 such as a carbonyl group; methoxycarbonylmethoxy group, ethoxycarbonylmethoxy group, and third butoxy group An alkoxycarbonylalkoxy group having 3 to 6 carbon atoms such as a carbonylmethoxy group; a halogen atom such as fluorine or chlorine; or a fluoroalkyl group such as a fluoromethyl group, a trifluoromethyl group or a pentafluoroethyl group.
上述式(16)中的A6與A7相互連結而形成的環優選列舉芳香環、碳數為2~20的飽和或不飽和的含氮雜環。A6與A7相互連結而形成的環為苯環的情況時的含有咪唑環的化合物可列舉下述式(17)所表示的化合物。 The ring formed by linking A 6 and A 7 in the above formula (16) to each other is preferably an aromatic ring or a saturated or unsaturated nitrogen-containing hetero ring having 2 to 20 carbon atoms. A compound represented by the following formula (17) is exemplified as the imidazole ring-containing compound in the case where the ring formed by the combination of A 6 and A 7 is a benzene ring.
在上述式(17)中,R48及A5與上述式(16)同義。R49~R52分別獨立為亦可具有取代基的碳數為1~20的直鏈狀、分支狀或環狀的烴基。另外,R49~R52所表示的烴基可列舉與上述式(16)中的烴基同樣的基。 In the above formula (17), R 48 and A 5 are synonymous with the above formula (16). R 49 to R 52 are each independently a linear, branched or cyclic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. Further, examples of the hydrocarbon group represented by R 49 to R 52 include the same groups as those of the hydrocarbon group in the above formula (16).
含有咪唑環的化合物優選為2-苯基苯並咪唑、2-甲基咪唑、2-甲基苯並咪唑。含有咪唑環的化合物可單獨使用或者將2種以上混合使用。作為含有咪唑環的化合物的含有比例,相對於[I]鹼溶性樹脂100質量份而言優選為0.1質量份~10質量份,更優選為0.5質量份~5質量份。通 過使含有咪唑環的化合物的含有比例為上述特定範圍,能夠以更高的水準兼顧著色組成物的保存穩定性與低溫硬化。 The imidazole ring-containing compound is preferably 2-phenylbenzimidazole, 2-methylimidazole or 2-methylbenzimidazole. The compound containing an imidazole ring may be used singly or in combination of two or more. The content ratio of the imidazole ring-containing compound is preferably 0.1 parts by mass to 10 parts by mass, more preferably 0.5 parts by mass to 5 parts by mass, per 100 parts by mass of the [I] alkali-soluble resin. through When the content ratio of the compound containing an imidazole ring is within the above specific range, the storage stability of the colored composition and the low-temperature curing can be achieved at a higher level.
本實施形態的彩色濾光片製造中所使用的著色組成物除了上述[I]鹼溶性樹脂、[II]聚合性化合物、[III]聚合起始劑、[IV]著色劑、及[V]化合物(硬化劑)以外,還可以在不損及本發明的效果的範圍內視需要含有界面活性劑、保存穩定劑、接著助劑、耐熱性促進劑等其他任意成分。該些各任意成分可單獨使用亦可混合使用2種以上。以下對各成分加以詳述。 In addition to the above [I] alkali-soluble resin, [II] polymerizable compound, [III] polymerization initiator, [IV] colorant, and [V], the coloring composition used in the production of the color filter of the present embodiment. In addition to the compound (hardener), other optional components such as a surfactant, a storage stabilizer, a bonding aid, and a heat resistance promoter may be contained as needed within a range that does not impair the effects of the present invention. These optional components may be used singly or in combination of two or more. The components are detailed below.
界面活性劑可用以使著色組成物的塗膜形成性進一步提高。界面活性劑例如可列舉氟類界面活性劑、矽酮類界面活性劑及其他界面活性劑。 The surfactant can be used to further improve the coating film formability of the colored composition. Examples of the surfactant include a fluorine-based surfactant, an anthrone-based surfactant, and other surfactants.
氟類界面活性劑優選在末端、主鏈及側鏈的至少任意部位具有氟烷基及/或氟伸烷基的化合物。 The fluorine-based surfactant is preferably a compound having a fluoroalkyl group and/or a fluorine alkyl group at at least any part of the terminal, the main chain and the side chain.
氟類界面活性劑的市售品例如可列舉Ftergent(注冊商標)FT-100、Ftergent FT-110、Ftergent FT-140A、Ftergent FT-150、Ftergent FT-250、Ftergent FT-251、Ftergent FT-300、Ftergent FT-310、Ftergent FT-400S、Ftergent(注冊商標)FTX-218、Ftergent FTX-251(以上由Neos公司製造)等。 Commercial products of the fluorine-based surfactant include, for example, Ftergent (registered trademark) FT-100, Ftergent FT-110, Ftergent FT-140A, Ftergent FT-150, Ftergent FT-250, Ftergent FT-251, and Ftergent FT-300. Ftergent FT-310, Ftergent FT-400S, Ftergent (registered trademark) FTX-218, Ftergent FTX-251 (above manufactured by Neos), and the like.
矽酮類界面活性劑的市售品例如可列舉Toray Silicone DC3PA、Toray Silicone DC7PA、Toray Silicone SH11PA、Toray Silicone SH21PA、Toray Silicone SH28PA、Toray Silicone SH29PA、Toray Silicone SH30PA、Toray Silicone SH-190、Toray Silicone SH-193、Toray Silicone SZ-6032、Toray Silicone SF-8428、Toray Silicone DC-57、Toray Silicone DC-190(以上由道康寧東麗矽膠公司(Dow Corning Toray Silicone Co.,Ltd.)製造)等。 A commercially available product of an anthrone-based surfactant can be exemplified by Toray. Silicone DC3PA, Toray Silicone DC7PA, Toray Silicone SH11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH-190, Toray Silicone SH-193, Toray Silicone SZ-6032, Toray Silicone SF-8428 Toray Silicone DC-57, Toray Silicone DC-190 (above manufactured by Dow Corning Toray Silicone Co., Ltd.) and the like.
作為界面活性劑的使用量,相對於[I]鹼溶性樹脂100質量份而言優選為1.0質量份以下,更優選為0.7質量份以下。若界面活性劑的使用量超過1.0質量份,則變得容易產生膜不均。 The amount of the surfactant to be used is preferably 1.0 part by mass or less, and more preferably 0.7 part by mass or less based on 100 parts by mass of the [I] alkali-soluble resin. When the amount of the surfactant used exceeds 1.0 part by mass, film unevenness is likely to occur.
保存穩定劑例如可列舉硫、醌類、對苯二酚類、聚氧化合物、胺、硝基亞硝基化合物等,更具體而言可列舉4-甲氧基苯酚、N-亞硝基-N-苯基羥胺鋁等。 Examples of the storage stabilizer include sulfur, hydrazines, hydroquinones, polyoxygen compounds, amines, nitronitroso compounds, and the like, and more specifically, 4-methoxyphenol and N-nitroso- N-phenylhydroxylamine aluminum and the like.
作為保存穩定劑的使用量,相對於[I]鹼溶性樹脂100質量份而言優選為3.0質量份以下,更優選為1.0質量份以下。若保存穩定劑的調配量超過3.0質量份,則存在感光度降低而造成圖案形狀劣化的情況。 The amount of use as the storage stabilizer is preferably 3.0 parts by mass or less, and more preferably 1.0 parts by mass or less, based on 100 parts by mass of the [I] alkali-soluble resin. When the amount of the stabilizer to be added exceeds 3.0 parts by mass, the sensitivity may be lowered to deteriorate the pattern shape.
接著助劑可用以使所得的著色圖案及彩色濾光片與基板的接著性進一步提高。接著助劑優選具有羧基、甲基丙烯醯基、乙烯基、異氰酸酯基、環氧乙烷基等反應性官能基的官能性矽烷偶聯劑,例如可列舉三甲氧基矽烷基苯 甲酸、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、乙烯基三乙醯氧基矽烷、乙烯基三甲氧基矽烷、γ-異氰酸酯基丙基三乙氧基矽烷、γ-縮水甘油氧基丙基三甲氧基矽烷、β-(3,4-環氧環己基)乙基三甲氧基矽烷等。 The additive can then be used to further improve the adhesion of the resulting colored pattern and color filter to the substrate. The auxiliary agent is preferably a functional decane coupling agent having a reactive functional group such as a carboxyl group, a methacryloyl group, a vinyl group, an isocyanate group or an oxiranyl group, and examples thereof include trimethoxynonylbenzene. Formic acid, γ-methyl propylene methoxy propyl trimethoxy decane, vinyl triethoxy decane, vinyl trimethoxy decane, γ-isocyanate propyl triethoxy decane, γ-glycidyl oxygen Propyltrimethoxydecane, β-(3,4-epoxycyclohexyl)ethyltrimethoxydecane, and the like.
作為接著助劑的使用量,相對於[I]鹼溶性樹脂100質量份而言優選為20質量份以下,更優選為15質量份以下。若接著助劑的使用量超過20質量份,則存在變得容易產生顯影殘留的傾向。 The amount of the auxiliary agent to be used is preferably 20 parts by mass or less, and more preferably 15 parts by mass or less, based on 100 parts by mass of the [I] alkali-soluble resin. When the amount of the auxiliary agent used exceeds 20 parts by mass, the development residue tends to be likely to occur.
本實施形態的彩色濾光片製造中所使用的著色組成物可通過將[I]鹼溶性樹脂、[II]聚合性化合物、[III]聚合起始劑、[IV]著色劑、[V]化合物(硬化劑)、及視需要而添加的其他任意成分均一混合而調製。該著色組成物優選溶解於適當的溶劑中而以溶液狀使用。 The coloring composition used in the production of the color filter of the present embodiment can be obtained by using [I] an alkali-soluble resin, [II] a polymerizable compound, [III] a polymerization initiator, [IV] a colorant, [V]. The compound (hardener) and other optional components added as needed are uniformly mixed and prepared. The coloring composition is preferably dissolved in a suitable solvent and used in the form of a solution.
作為著色組成物的調製中所使用的溶劑,使用可均一地溶解必需成分及任意成分且不與各成分反應的溶劑。此種溶劑可列舉與上述的作為可用於製造[I]鹼溶性樹脂的溶劑而例示者相同的溶劑。 As a solvent used for preparation of a coloring composition, a solvent which can uniformly dissolve an essential component and an arbitrary component and does not react with each component is used. Examples of such a solvent include the same solvents as those exemplified above as the solvent which can be used for producing the [I] alkali-soluble resin.
該些溶劑中,自各成分的溶解性、與各成分的反應性、塗膜形成的容易性等觀點考慮,例如可列舉:乙二醇單甲醚、乙二醇單乙醚、乙二醇單正丙醚、乙二醇單正丁醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇單正丙醚、二乙二醇單正丁醚、三乙二醇單甲醚、三乙二醇單乙醚、丙二醇單甲醚、丙二醇單乙醚、丙二醇單正丙醚、丙 二醇單正丁醚、二丙二醇單甲醚、二丙二醇單乙醚、二丙二醇單正丙醚、二丙二醇單正丁醚、三丙二醇單甲醚、三丙二醇單乙醚等(聚)烷二醇單烷基醚類;乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、乙二醇單正丙醚乙酸酯、乙二醇單正丁醚乙酸酯、二乙二醇單甲醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單正丙醚乙酸酯、二乙二醇單正丁醚乙酸酯、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、乙酸-3-甲氧基丁酯、乙酸-3-甲基-3-甲氧基丁酯等(聚)烷二醇單烷基醚乙酸酯類;二乙二醇二甲醚、二乙二醇甲乙醚、二乙二醇二乙醚、四氫呋喃等其他醚類;丁酮、環己酮、2-庚酮、3-庚酮、二丙酮醇(4-羥基-4-甲基戊烷-2-酮)、4-羥基-4-甲基己烷-2-酮等酮類;丙二醇二乙酸酯、1,3-丁二醇二乙酸酯、1,6-己二醇二乙酸酯等二乙酸酯類;乳酸甲酯、乳酸乙酯等乳酸烷基酯類;乙酸乙酯、乙酸正丙酯、乙酸異丙酯、乙酸正丁酯、乙酸異丁酯、甲酸正戊酯、乙酸異戊酯、乙酸-3-甲氧基丁酯、乙酸-3-甲基-3-甲氧基丁酯、丙酸正丁酯、乙酸-3-甲氧基丁酯、丙酸-3-甲基-3-甲氧基丁酯、丁酸乙酯、丁酸正丙酯、丁酸異丙酯、丁酸正丁酯、羥基乙酸乙酯、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、丙酮酸甲酯、丙酮酸乙酯、丙酮酸正丙酯、乙醯乙酸甲酯、乙醯乙酸乙酯、2- 羥基-2-甲基丙酸乙酯、2-羥基-3-甲基丁酸甲酯、2-氧代丁酸乙基等其他酯類;甲苯、二甲苯等芳香族烴類;N-甲基吡咯烷酮、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等醯胺類等。 Among these solvents, from the viewpoints of solubility of each component, reactivity with each component, easiness of formation of a coating film, and the like, for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and ethylene glycol single positive are exemplified. Propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl Ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, C Glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether (poly) alkanediol single Alkyl ethers; ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol mono-n-propyl ether acetate, ethylene glycol mono-n-butyl ether acetate, diethylene glycol Monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol mono-n-propyl ether acetate, diethylene glycol mono-n-butyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol (poly)alkylene glycol monoalkyl ether acetates such as monoethyl ether acetate, acetic acid-3-methoxybutyl ester, acetic acid-3-methyl-3-methoxybutyl ester; diethylene glycol II Other ethers such as methyl ether, diethylene glycol methyl ether, diethylene glycol diethyl ether, tetrahydrofuran; butanone, cyclohexanone, 2-heptanone, 3-heptanone, diacetone alcohol (4-hydroxy-4- Ketones such as methylpentan-2-one) and 4-hydroxy-4-methylhexane-2-one; propylene glycol diacetate, 1,3-butanediol diacetate, 1,6- Diacetate such as hexanediol diacetate; lactate such as methyl lactate or ethyl lactate Base esters; ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-amyl formate, isoamyl acetate, 3-methoxybutyl acetate, acetic acid - 3-methyl-3-methoxybutyl ester, n-butyl propionate,-3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl butyrate, N-propyl butyrate, isopropyl butyrate, n-butyl butyrate, ethyl hydroxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, Methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetate, ethyl acetate, 2- Other esters such as ethyl hydroxy-2-methylpropionate, methyl 2-hydroxy-3-methylbutanoate, ethyl 2-oxobutanoate; aromatic hydrocarbons such as toluene and xylene; N-A Amidoxime such as pyrrolidone, N,N-dimethylformamide or N,N-dimethylacetamide.
該些溶劑中,自溶解性、顏料分散性、塗布性等觀點考慮,優選為丙二醇單甲醚、丙二醇單乙醚、乙二醇單甲醚乙酸酯、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、乙酸-3-甲氧基丁酯、二乙二醇二甲醚、二乙二醇甲乙醚、環己酮、2-庚酮、3-庚酮、1,3-丁二醇二乙酸酯、1,6-己二醇二乙酸酯、乳酸乙酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、丙酸-3-甲基-3-甲氧基丁基酯、乙酸正丁酯、乙酸異丁酯、甲酸正戊酯、乙酸異戊酯、丙酸正丁酯、丁酸乙酯、丁酸異丙酯、丁酸正丁酯、丙酮酸乙酯。溶劑可單獨使用或使用2種以上。 Among these solvents, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, and propylene glycol are preferable from the viewpoints of solubility, pigment dispersibility, and coating properties. Ethyl acetate, 3-methoxybutyl acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 2-heptanone, 3-heptanone, 1,3-butane Alcohol diacetate, 1,6-hexanediol diacetate, ethyl lactate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxypropionic acid Ester, 3-methyl-3-methoxybutyl propionate, n-butyl acetate, isobutyl acetate, n-amyl formate, isoamyl acetate, n-butyl propionate, ethyl butyrate, Isopropyl butyrate, n-butyl butyrate, ethyl pyruvate. The solvent may be used singly or in combination of two or more.
另外,亦可與上述溶劑一同併用苄基乙基醚、二正己基醚、丙酮基丙酮、異佛爾酮、己酸、辛酸、1-辛醇、1-壬醇、乙酸苄基酯、苯甲酸乙酯、乙二酸二乙酯、馬來酸二乙酯、γ-丁內酯、碳酸乙二酯、碳酸丙二酯、乙二醇單苯醚乙酸酯等高沸點溶劑。上述高沸點溶劑可單獨使用或使用2種以上。 In addition, together with the above solvent, benzyl ethyl ether, di-n-hexyl ether, acetone acetone, isophorone, hexanoic acid, octanoic acid, 1-octanol, 1-nonanol, benzyl acetate, benzene may also be used together. A high boiling point solvent such as ethyl formate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate or ethylene glycol monophenyl ether acetate. These high boiling point solvents may be used singly or in combination of two or more.
溶劑的含量並無限定,自所得的著色組成物的塗布性、穩定性等觀點考慮,除去著色組成物的溶劑的各成分的合計濃度優選成為5質量%~50質量%的量,更優選成 為10質量%~40質量%的量。在將著色組成物調製為溶液狀態的情況時,固形物濃度(組成物溶液中所占的溶劑以外的成分)可根據使用目的或所期望的膜厚的值等而設定為任意濃度(例如5質量%~50質量%)。更優選的固形物濃度根據在基板上形成塗膜的形成方法而有所不同,於後文對其加以敍述。如此而調製的組成物溶液可使用孔徑為0.5 μm左右的微孔過濾器等而進行過濾後,供至使用。 The content of the solvent is not limited, and the total concentration of each component of the solvent in which the coloring composition is removed is preferably from 5% by mass to 50% by mass, more preferably from the viewpoint of the coating property and stability of the obtained colored composition. It is an amount of 10% by mass to 40% by mass. When the coloring composition is prepared in a solution state, the solid content concentration (component other than the solvent in the composition solution) can be set to an arbitrary concentration depending on the purpose of use or a desired film thickness or the like (for example, 5) Mass%~50% by mass). A more preferable solid content concentration differs depending on a method of forming a coating film on a substrate, which will be described later. The composition solution prepared in this manner can be filtered using a micropore filter having a pore diameter of about 0.5 μm, and then used.
以上成分與調製方法的著色組成物可利用低溫硬化而形成著色圖案。具體而言,即使在200℃以下的硬化溫度下、進一步在180℃以下的硬化溫度下,亦可獲得具有耐溶劑性等良好的可靠性的著色圖案。而且,可利用低溫硬化而提供本實施形態的彩色濾光片。 The coloring composition of the above components and the preparation method can be cured by low temperature to form a colored pattern. Specifically, even at a curing temperature of 200 ° C or lower and further at a curing temperature of 180 ° C or lower, a colored pattern having good reliability such as solvent resistance can be obtained. Further, the color filter of the present embodiment can be provided by low-temperature curing.
其次,本實施形態的彩色濾光片可以在著色圖案上設置保護膜。該保護膜使用感放射線性樹脂組成物而形成在著色圖案上。而且,保護膜具有如下功能:覆蓋著色圖案而對其中所含有的染料等著色劑進行保護,且實現於其上所形成的透明電極的優異的特性。以下,對本實施形態的彩色濾光片的保護膜的形成中所使用的本實施形態的感放射線性樹脂組成物加以說明。 Next, the color filter of this embodiment can be provided with a protective film on the colored pattern. The protective film is formed on the colored pattern using a radiation sensitive resin composition. Further, the protective film has a function of protecting the coloring agent such as a dye contained therein by covering the colored pattern, and achieving excellent characteristics of the transparent electrode formed thereon. Hereinafter, the radiation sensitive resin composition of the present embodiment used for forming the protective film of the color filter of the present embodiment will be described.
本實施形態的彩色濾光片的保護膜的形成中所使用的本實施形態的感放射線性樹脂組成物含有[A]化合物、[B]聚合性化合物、[C]聚合起始劑及[D]化合物,且亦可進一步含有任意成分。感放射線性樹脂組成物可通過利用感放 射線性的曝光、顯影而容易地形成微細且精巧的圖案,從而實現低溫硬化。而且,具有保存穩定性且具有充分的分辨率及放射線感光度。以下對各成分加以詳述。 The radiation sensitive resin composition of the present embodiment used for forming the protective film of the color filter of the present embodiment contains the [A] compound, the [B] polymerizable compound, the [C] polymerization initiator, and [D]. The compound may further contain an optional component. Radiation-sensitive resin composition can be utilized by using Radiation exposure and development easily form a fine and delicate pattern to achieve low temperature hardening. Moreover, it has storage stability and has sufficient resolution and radiation sensitivity. The components are detailed below.
本實施形態的感放射線性樹脂組成物中所含有的[A]化合物是具有環氧基的化合物。[A]化合物例如可列舉在1分子內具有2個以上3,4-環氧環己基的化合物等。 The compound [A] contained in the radiation sensitive resin composition of the present embodiment is a compound having an epoxy group. The compound [A] may, for example, be a compound having two or more 3,4-epoxycyclohexyl groups in one molecule.
在1分子內具有2個以上3,4-環氧環己基的化合物例如可列舉3,4-環氧環己基甲基-3',4'-環氧環己烷甲酸酯、2-(3,4-環氧環己基-5,5-螺-3,4-環氧)環己烷-間二噁烷、雙(3,4-環氧環己基甲基)己二酸酯、雙(3,4-環氧-6-甲基環己基甲基)己二酸酯、3,4-環氧-6-甲基環己基-3',4'-環氧-6'-甲基環己烷甲酸酯、亞甲基雙(3,4-環氧環己烷)、二環戊二烯二環氧化物、乙二醇的二(3,4-環氧環己基甲基)醚、乙撐雙(3,4-環氧環己烷甲酸)酯、內酯改質3,4-環氧環己基甲基-3',4'-環氧環己烷甲酸酯等。 Examples of the compound having two or more 3,4-epoxycyclohexyl groups in one molecule include 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexane formate, 2-( 3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane-m-dioxane, bis(3,4-epoxycyclohexylmethyl)adipate, double (3,4-epoxy-6-methylcyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexyl-3',4'-epoxy-6'-methyl Cyclohexanecarboxylate, methylene bis(3,4-epoxycyclohexane), dicyclopentadiene diepoxide, ethylene glycol bis(3,4-epoxycyclohexylmethyl) Ether, ethylene bis(3,4-epoxycyclohexanecarboxylic acid) ester, lactone modified 3,4-epoxycyclohexylmethyl-3', 4'-epoxycyclohexane formate, and the like.
其他[A]化合物例如可列舉:雙酚A二縮水甘油醚、雙酚F二縮水甘油醚、雙酚S二縮水甘油醚、氫化雙酚A二縮水甘油醚、氫化雙酚F二縮水甘油醚、氫化雙酚AD二縮水甘油醚、溴化雙酚A二縮水甘油醚、溴化雙酚F二縮水甘油醚、溴化雙酚S二縮水甘油醚等雙酚化合物的二縮水甘油醚;1,4-丁二醇二縮水甘油醚、1,6-己二醇二縮水甘油醚、甘油三縮水甘油醚、三羥甲基丙烷三縮水甘油醚、聚乙二 醇二縮水甘油醚、聚丙二醇二縮水甘油醚等多元醇的聚縮水甘油醚;通過在乙二醇、丙二醇、丙三醇等脂肪族多元醇上加成1種或2種以上環氧烷而所得的聚醚多元醇的聚縮水甘油醚;苯酚酚醛型環氧樹脂;甲酚酚醛型環氧樹脂;多酚型環氧樹脂;環狀脂肪族環氧樹脂;脂肪族長鏈二元酸的二縮水甘油酯;高級脂肪酸的縮水甘油酯;環氧化大豆油、環氧化亞麻籽油等。 Examples of the other [A] compound include bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether. a diglycidyl ether of a bisphenol compound such as hydrogenated bisphenol AD diglycidyl ether, brominated bisphenol A diglycidyl ether, brominated bisphenol F diglycidyl ether or brominated bisphenol S diglycidyl ether; , 4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerol triglycidyl ether, trimethylolpropane triglycidyl ether, polyethylene a polyglycidyl ether of a polyhydric alcohol such as an alcohol diglycidyl ether or a polypropylene glycol diglycidyl ether; or a method of adding one or more alkylene oxides to an aliphatic polyol such as ethylene glycol, propylene glycol or glycerin; Polyglycidyl ether of the obtained polyether polyol; phenol novolak type epoxy resin; cresol novolac type epoxy resin; polyphenol type epoxy resin; cyclic aliphatic epoxy resin; aliphatic long chain dibasic acid Glycidyl ester; glycidyl ester of higher fatty acid; epoxidized soybean oil, epoxidized linseed oil, and the like.
作為該些的市售品,例如:雙酚A型環氧樹脂可列舉Epikote 1001、Epikote 1002、Epikote 1003、Epikote 1004、Epikote 1007、Epikote 1009、Epikote 1010、Epikote 828(以上由日本環氧樹脂公司(Japan Epoxy Resins Co.,Ltd)製造)等;雙酚F型環氧樹脂可列舉Epikote 807(日本環氧樹脂公司)等;苯酚酚醛型環氧樹脂可列舉Epikote 152、Epikote 154、Epikote 157S65(以上由日本環氧樹脂公司製造)、EPPN 201、EPPN 202(以上由日本化藥公司製造)等;甲酚酚醛型環氧樹脂可列舉EOCN(注冊商標)102、EOCN 103S、EOCN 104S、EOCN 1020、EOCN 1025、 EOCN 1027(以上由日本化藥公司製造)、Epikote 180S75(日本環氧樹脂公司)等;多酚型環氧樹脂可列舉Epikote 1032H60、Epikote XY-4000(以上由日本環氧樹脂公司製造)等;環狀脂肪族環氧樹脂可列舉CY-175、CY-177、CY-179、Araldite CY-182、Araldite CY-192、Araldite CY-184(以上由汽巴精化有限公司製造)、ERL-4234、ERL-4299、ERL-4221、ERL-4206(以上由U.C.C公司製造)、Shodyne 509(昭和電工公司)、Epiclon 200、Epiclon 400(以上由大日本油墨公司製造)、Epikote 871、Epikote 872(以上由日本環氧樹脂公司製造)、ED-5661、ED-5662(以上由Celanese coating公司製造)等;脂肪族聚縮水甘油醚可列舉Epolight 100MF(共榮社化學公司)、EPIOL TMP(日本油脂公司)等。 As such commercially available products, for example, bisphenol A type epoxy resin includes Epikote 1001, Epikote 1002, Epikote 1003, Epikote 1004, Epikote 1007, Epikote 1009, Epikote 1010, and Epikote 828 (above by Japanese epoxy resin company) (manufactured by Japan Epoxy Resins Co., Ltd.); bisphenol F-type epoxy resin: Epikote 807 (Nippon Epoxy Co., Ltd.); and phenol novolac type epoxy resin; Epikote 152, Epikote 154, Epikote 157S65 ( The above is manufactured by Japan Epoxy Resin Co., Ltd., EPPN 201, EPPN 202 (manufactured by Nippon Kayaku Co., Ltd.), etc.; cresol novolac type epoxy resin can be listed as EOCN (registered trademark) 102, EOCN 103S, EOCN 104S, EOCN 1020 EOCN 1025, EOCN 1027 (manufactured by Nippon Kayaku Co., Ltd.), Epikote 180S75 (Nippon Epoxy Co., Ltd.), etc.; and polyphenol type epoxy resin, such as Epikote 1032H60 and Epikote XY-4000 (above, manufactured by Nippon Epoxy Co., Ltd.); Examples of the cyclic aliphatic epoxy resin include CY-175, CY-177, CY-179, Araldite CY-182, Araldite CY-192, Araldite CY-184 (above, manufactured by Ciba Specialty Chemicals Co., Ltd.), and ERL-4234. , ERL-4299, ERL-4221, ERL-4206 (above manufactured by UCC), Shodyne 509 (Showa Denko), Epiclon 200, Epiclon 400 (above manufactured by Dainippon Ink Co., Ltd.), Epikote 871, Epikote 872 (above) Manufactured by Japan Epoxy Resin Co., Ltd., ED-5661, ED-5662 (manufactured by Celanese Coating Co., Ltd.), etc.; aliphatic polyglycidyl ethers include Epolight 100MF (Kyoeisha Chemical Co., Ltd.) and EPIOL TMP (Japan Oil & Fats Co., Ltd.) )Wait.
該些中優選苯酚酚醛型環氧樹脂及多酚型環氧樹脂。 Among these, a phenol novolak type epoxy resin and a polyphenol type epoxy resin are preferable.
上述所例示的[A]化合物與後述的作為具有羧基的共聚物的[A]化合物一同含有於感放射線性組成物中的情形時,作為上述所例示的[A]化合物的使用量,相對於後述的作為具有羧基的共聚物的[A]化合物100質量份而言,優選為50質量份以下,更優選為30質量份以下,特別優選為2質量份~15質量份的範圍內。 When the compound [A] exemplified above is contained in the radiation sensitive composition together with the compound [A] which is a copolymer having a carboxyl group to be described later, the amount of the compound [A] exemplified above is relative to 100 parts by mass of the compound [A] which is a copolymer having a carboxyl group, which is described later, is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, and particularly preferably 2 parts by mass to 15 parts by mass.
[A]化合物優選為聚合物,更優選該聚合物進一步具有羧基。而且,[A]化合物更優選具有羧基的共聚物。[A]化合物具有具羧基的結構,因此感放射線性樹脂組成物可 形成耐熱性、耐光性、耐化學品性、透射率、平坦性等更優異的硬化膜。 The compound [A] is preferably a polymer, and more preferably the polymer further has a carboxyl group. Further, the compound [A] is more preferably a copolymer having a carboxyl group. [A] The compound has a structure having a carboxyl group, and thus the radiation sensitive resin composition can be A cured film having more excellent heat resistance, light resistance, chemical resistance, transmittance, flatness, and the like is formed.
[A]化合物可使用包含由選自不飽和羧酸及不飽和羧酸酐所構成的群組的至少1種所形成的結構單元、以及由含有環氧基的不飽和化合物所形成的結構單元的共聚物。在這種情況下,[A]化合物可使用與上述本實施形態的著色組成物中所含有的[I]鹼溶性樹脂相同的共聚物。例如可使用上述(I-1)選自由不飽和羧酸及不飽和羧酸酐所構成的群組的至少1種((I-1)化合物)與(I-2)含有環氧基的不飽和化合物((I-2)化合物)共聚而成的鹼溶性樹脂。 The [A] compound may be a structural unit formed of at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and structural units formed of an epoxy group-containing unsaturated compound. Copolymer. In this case, as the [A] compound, the same copolymer as the [I] alkali-soluble resin contained in the coloring composition of the above-described embodiment can be used. For example, (I-1) at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides ((I-1) compound) and (I-2) epoxy group-containing unsaturated group can be used. An alkali-soluble resin obtained by copolymerizing a compound ((I-2) compound).
[B]聚合性化合物是具有乙烯性不飽和鍵的聚合性化合物。[B]聚合性化合物可使用與上述本實施形態的著色組成物中所含有的[II]聚合性化合物相同的化合物。 [B] The polymerizable compound is a polymerizable compound having an ethylenically unsaturated bond. [B] The polymerizable compound can be the same compound as the [II] polymerizable compound contained in the coloring composition of the above-described embodiment.
[B]聚合性化合物可單獨使用或者將2種以上混合使用。作為感放射線性樹脂組成物中的[B]聚合性化合物的含有比例,相對於作為具有羧基的共聚物的[A]化合物100質量份而言優選為20質量份~200質量份,更優選為40質量份~160質量份。通過使[B]聚合性化合物的含有比例為上述範圍,感放射線性樹脂組成物可形成密接性優異且即使於低曝光量下亦具有充分的硬度的硬化膜,且可提供優異的保護膜。 [B] The polymerizable compound may be used singly or in combination of two or more. The content ratio of the [B] polymerizable compound in the radiation sensitive resin composition is preferably 20 parts by mass to 200 parts by mass, more preferably 100 parts by mass to 200 parts by mass of the [A] compound which is a copolymer having a carboxyl group. 40 parts by mass to 160 parts by mass. When the content ratio of the [B] polymerizable compound is in the above range, the radiation-sensitive resin composition can form a cured film which is excellent in adhesion and has sufficient hardness even at a low exposure amount, and can provide an excellent protective film.
[C]聚合起始劑是感放射線性聚合起始劑,是可感應放 射線而產生能夠引發聚合反應的活性種的成分。可使用與上述的本實施形態的著色組成物中所含有的[III]聚合起始劑相同的化合物。 [C] The polymerization initiator is a radiation-sensitive polymerization initiator, which can be inductively placed. The ray produces a component of the active species capable of initiating a polymerization reaction. The same compound as the [III] polymerization initiator contained in the coloring composition of the present embodiment described above can be used.
[C]聚合起始劑可單獨使用或者將2種以上混合使用。作為感放射線性樹脂組成物中的[C]聚合起始劑的含有比例,相對於作為具有羧基的共聚物的[A]化合物100質量份而言,優選為1質量份~40質量份,更優選為5質量份~30質量份。通過使[C]聚合起始劑的含有比例為1質量份~40質量份,感放射線性樹脂組成物即使在低曝光量的情況時亦可形成具有高的硬度及密接性的硬化膜,可提供優異的保護膜。 [C] The polymerization initiator may be used singly or in combination of two or more. The content ratio of the [C] polymerization initiator in the radiation-sensitive resin composition is preferably 1 part by mass to 40 parts by mass, based on 100 parts by mass of the [A] compound which is a copolymer having a carboxyl group. It is preferably 5 parts by mass to 30 parts by mass. When the content ratio of the [C] polymerization initiator is from 1 part by mass to 40 parts by mass, the radiation-sensitive resin composition can form a cured film having high hardness and adhesion even at a low exposure amount. Provides an excellent protective film.
本實施形態的彩色濾光片的保護膜的形成中所使用的感放射線性樹脂組成物可通過含有具有胺基與吸電子基的[D]化合物而實現感放射線性樹脂組成物的低溫硬化時的硬化膜的硬化促進。而且,亦可實現保存穩定性,另外能夠以高的水準而保持包含彩色濾光片(所述彩色濾光片具有所得的硬化膜)的液晶顯示元件的電壓保持率。 The radiation-sensitive resin composition used for forming the protective film of the color filter of the present embodiment can achieve low-temperature hardening of the radiation-sensitive resin composition by containing the [D] compound having an amine group and an electron-withdrawing group. The hardening of the hardened film is promoted. Further, storage stability can be achieved, and the voltage holding ratio of the liquid crystal display element including the color filter (the color filter having the obtained cured film) can be maintained at a high level.
[D]化合物是選自由上述式(1)及式(2)所表示的化合物所構成的群組的至少1種化合物。關於上述式(1)及式(2)所表示的化合物的結構的詳細,在說明上述著色組成物中所含有的[V]化合物時已進行了說明。因此,在式(2)中,R7~R16中的至少1個是胺基,該胺基的氫原子的全部或一部分亦可被碳數為1~6的烴基取代,在為感放 射線性樹脂組成物中所使用的[D]化合物的情況時,該胺基的氫原子的全部或一部分亦可被碳數為2~6的伸烷基取代。 The compound [D] is at least one compound selected from the group consisting of the compounds represented by the above formulas (1) and (2). The details of the structures of the compounds represented by the above formulas (1) and (2) have been described in the description of the [V] compound contained in the above colored composition. Therefore, in the formula (2), at least one of R 7 to R 16 is an amine group, and all or a part of the hydrogen atom of the amine group may be substituted by a hydrocarbon group having 1 to 6 carbon atoms, which is radiation sensitive. In the case of the [D] compound used in the resin composition, all or a part of the hydrogen atom of the amine group may be substituted with an alkylene group having 2 to 6 carbon atoms.
作為[D]化合物,優選為2,2-雙(4-胺基苯基)六氟丙烷、2,3-雙(4-胺基苯基)丁二腈、4,4'-二胺基二苯甲酮、4,4'-二胺基苯甲酸苯酯、4,4'-二胺基二苯基碸、1,4-二胺基-2-氯苯、1,4-二胺基-2-溴苯、1,4-二胺基-2-碘苯、1,4-二胺基-2-硝基苯、1,4-二胺基-2-三氟甲基苯、2,5-二胺基苄腈、2,5-二胺基苯乙酮、2,5-二胺基苯甲酸、2,2'-二氯聯苯胺、2,2'-二溴聯苯胺、2,2,-二碘聯苯胺、2,2'-二硝基聯苯胺、2,2'-雙(三氟甲基)聯苯胺、3-胺基苯磺酸乙酯、3,5-雙三氟甲基-1,2-二胺基苯、4-胺基硝基苯、N,N-二甲基-4-硝基苯胺,更優選為4,4'-二胺基二苯基碸、2,2-雙(4-胺基苯基)六氟丙烷、2,2'-雙(三氟甲基)聯苯胺、3-胺基苯磺酸乙酯、3,5-雙三氟甲基-1,2-二胺基苯、4-胺基硝基苯、N,N-二甲基-4-硝基苯胺。 As the [D] compound, 2,2-bis(4-aminophenyl)hexafluoropropane, 2,3-bis(4-aminophenyl)succinonitrile, 4,4'-diamino group are preferable. Benzophenone, phenyl 4,4'-diaminobenzoate, 4,4'-diaminodiphenylanthracene, 1,4-diamino-2-chlorobenzene, 1,4-diamine 2-bromobenzene, 1,4-diamino-2-iodobenzene, 1,4-diamino-2-nitrobenzene, 1,4-diamino-2-trifluoromethylbenzene, 2,5-Diaminobenzonitrile, 2,5-diaminoacetophenone, 2,5-diaminobenzoic acid, 2,2'-dichlorobenzidine, 2,2'-dibromobenzidine , 2,2,-diiodobenzidine, 2,2'-dinitrobenzidine, 2,2'-bis(trifluoromethyl)benzidine, ethyl 3-aminobenzenesulfonate, 3,5 - bistrifluoromethyl-1,2-diaminobenzene, 4-aminonitrobenzene, N,N-dimethyl-4-nitroaniline, more preferably 4,4'-diaminodi Phenylhydrazine, 2,2-bis(4-aminophenyl)hexafluoropropane, 2,2'-bis(trifluoromethyl)benzidine, ethyl 3-aminobenzenesulfonate, 3,5- Bis-trifluoromethyl-1,2-diaminobenzene, 4-aminonitrobenzene, N,N-dimethyl-4-nitroaniline.
作為感放射線性樹脂組成物中的[D]化合物的含有比例,相對於作為具有羧基的共聚物的[A]化合物100質量份而言,優選為0.1質量份~20質量份,更優選為0.2質量份~10質量份。通過使[D]化合物的含有比例為0.1質量份~10質量份,可實現由感放射線性樹脂組成物而形成的保護膜的硬化促進。總之,使感放射線性樹脂組成物的保存穩定性提高,另外能夠以高的水準而保持包含彩色濾光片(所述彩色濾光片具有所得的保護膜)的液晶顯示元件的 電壓保持率。 The content ratio of the [D] compound in the radiation-sensitive resin composition is preferably 0.1 parts by mass to 20 parts by mass, more preferably 0.2% by mass based on 100 parts by mass of the [A] compound which is a copolymer having a carboxyl group. Parts by mass to 10 parts by mass. When the content ratio of the [D] compound is from 0.1 part by mass to 10 parts by mass, the curing of the protective film formed of the radiation sensitive resin composition can be promoted. In short, the storage stability of the radiation sensitive resin composition is improved, and the liquid crystal display element including the color filter (the color filter having the obtained protective film) can be held at a high level. Voltage retention rate.
本實施形態的感放射線性樹脂組成物除了上述[A]化合物、[B]聚合性化合物、[C]聚合起始劑、及[D]化合物以外,亦可在不損及所期望的效果的範圍內視需要而含有[J-1]接著助劑、[J-2]界面活性劑、[J-3]保存穩定劑及[J-4]耐熱性促進劑等任意成分。該些各任意成分可單獨使用亦可混合使用2種以上。以下,順次加以詳述。 In addition to the above [A] compound, [B] polymerizable compound, [C] polymerization initiator, and [D] compound, the radiation sensitive resin composition of the present embodiment may not impair the desired effect. Any components such as [J-1] adhesion aid, [J-2] surfactant, [J-3] storage stabilizer, and [J-4] heat resistance promoter are contained in the range as needed. These optional components may be used singly or in combination of two or more. Hereinafter, it will be described in detail.
[J-1]接著助劑可用以使所得的保護膜與基板的接著性進一步提高。此種[J-1]接著助劑可使用與上述的著色組成物的其他任意成分中的接著助劑相同的化合物。 [J-1] Next, an auxiliary agent can be used to further improve the adhesion of the obtained protective film to the substrate. Such a [J-1] adjunct additive may be the same compound as the adjunct agent in the other optional component of the coloring composition described above.
作為[J-1]接著助劑的使用量,相對於作為具有羧基的共聚物的[A]化合物100質量份而言,優選為20質量份以下,更優選為15質量份以下。若[J-1]接著助劑的使用量超過20質量份,則存在變得容易產生顯影殘留的傾向。 The amount of use of the [J-1]-based auxiliary agent is preferably 20 parts by mass or less, and more preferably 15 parts by mass or less, based on 100 parts by mass of the compound [A] which is a copolymer having a carboxyl group. When the amount of the auxiliary agent used in [J-1] exceeds 20 parts by mass, the development tends to be likely to occur.
[J-2]界面活性劑可用以使感放射線性樹脂組成物的塗膜形成性進一步提高。[J-2]界面活性劑例如可列舉氟類界面活性劑、矽酮類界面活性劑及其他界面活性劑,可使用與上述著色組成物的其他任意成分中的界面活性劑相同的化合物。 [J-2] The surfactant can be used to further improve the coating film formability of the radiation sensitive resin composition. [J-2] The surfactant may, for example, be a fluorine-based surfactant, an anthrone-based surfactant, or another surfactant, and a compound similar to the surfactant in any other component of the coloring composition described above may be used.
作為[J-2]界面活性劑的使用量,相對於作為具有羧基的共聚物的[A]化合物100質量份而言優選為1.0質量份以 下,更優選為0.8質量份以下。若[J-2]界面活性劑的使用量超過1.0質量份,則變得容易產生膜不均。 The amount of the surfactant used as the [J-2] is preferably 1.0 part by mass based on 100 parts by mass of the compound [A] which is a copolymer having a carboxyl group. Next, it is more preferably 0.8 parts by mass or less. When the amount of the [J-2] surfactant is more than 1.0 part by mass, film unevenness is likely to occur.
[J-3]保存穩定劑可使用與上述著色組成物的其他任意成分中的保存穩定劑相同的化合物,例如可列舉硫、醌類、對苯二酚類、聚氧化合物、胺、硝基亞硝基化合物等,更具體而言可列舉4-甲氧基苯酚、N-亞硝基-N-苯基羥胺鋁等。 [J-3] The storage stabilizer may be the same compound as the storage stabilizer in the other optional components of the above colored composition, and examples thereof include sulfur, anthraquinone, hydroquinone, polyoxyl compound, amine, and nitro group. Specific examples of the nitroso compound and the like include 4-methoxyphenol and N-nitroso-N-phenylhydroxylamine aluminum.
作為[J-3]保存穩定劑的使用量,相對於作為具有羧基的共聚物的[A]化合物100質量份而言,優選為3.0質量份以下,更優選為1.0質量份以下。若[J-3]保存穩定劑的調配量超過3.0質量份,則存在感放射線性樹脂組成物的感光度降低而造成圖案形狀劣化的情況。 The amount of use of the [J-3] storage stabilizer is preferably 3.0 parts by mass or less, and more preferably 1.0 part by mass or less, based on 100 parts by mass of the compound [A] which is a copolymer having a carboxyl group. When the amount of the [J-3] storage stabilizer is more than 3.0 parts by mass, the sensitivity of the radiation-sensitive resin composition may be lowered to deteriorate the pattern shape.
[J-4]耐熱性促進劑可使用與上述著色組成物的其他任意成分中的耐熱穩定劑相同的化合物。 [J-4] The heat resistance promoter may be the same compound as the heat resistant stabilizer in the other optional components of the above colored composition.
作為[J-4]耐熱性促進劑的使用量,相對於作為具有羧基的共聚物的[A]化合物100質量份而言優選為50質量份以下,更優選為30質量份以下。若[J-4]耐熱性促進劑的調配量超過50質量份,則存在感放射線性樹脂組成物的感光度降低而造成圖案形狀劣化的情況。 The amount of use of the heat resistance promoter of [J-4] is preferably 50 parts by mass or less, and more preferably 30 parts by mass or less, based on 100 parts by mass of the compound [A] which is a copolymer having a carboxyl group. When the amount of the heat-resistant accelerator of [J-4] exceeds 50 parts by mass, the sensitivity of the radiation-sensitive resin composition may be lowered to deteriorate the pattern shape.
本實施形態的感放射線性樹脂組成物可以通過如下方式而調製:將[A]化合物、[B]聚合性化合物、[C]聚合起 始劑及[D]化合物,以及在不損及所期望的效果的範圍內視需要的任意成分以規定比例加以混合。該感放射線性樹脂組成物優選溶解於適當的溶劑中而在溶液狀態下使用。 The radiation sensitive resin composition of the present embodiment can be prepared by polymerizing the [A] compound, the [B] polymerizable compound, and [C]. The starting agent and the [D] compound are mixed as needed in a predetermined ratio within a range that does not impair the desired effect. The radiation sensitive resin composition is preferably dissolved in a suitable solvent and used in a solution state.
感放射線性樹脂組成物的調製中所使用的溶劑可使用能夠均一地溶解或分散[A]化合物、[B]聚合性化合物、[C]聚合起始劑、[D]化合物及任意成分且不與各成分反應的溶劑。此種溶劑可列舉作為上述本實施形態的著色組成物的調製中所使用的溶劑而例示的溶劑。溶劑可單獨使用或者將2種以上混合使用。 The solvent used in the preparation of the radiation sensitive resin composition can be used to uniformly dissolve or disperse the [A] compound, the [B] polymerizable compound, the [C] polymerization initiator, the [D] compound, and the optional component, and A solvent that reacts with each component. The solvent is exemplified as the solvent used in the preparation of the coloring composition of the present embodiment. The solvent may be used singly or in combination of two or more.
作為感放射線性樹脂組成物的溶劑,當併用高沸點溶劑的情況時,其使用量相對於總溶劑量而言優選為50質量%以下,更優選為40質量%以下,特別優選為30質量%以下。當高沸點溶劑的使用量為50質量%以下時,塗膜的膜厚均一性、感光度及殘膜率變良好。 When the solvent of the radiation-sensitive linear resin composition is used in combination with a high-boiling solvent, the amount thereof is preferably 50% by mass or less, more preferably 40% by mass or less, and particularly preferably 30% by mass based on the total amount of the solvent. the following. When the amount of the high boiling point solvent used is 50% by mass or less, the film thickness uniformity, the sensitivity, and the residual film ratio of the coating film become good.
當將感放射線性樹脂組成物調製為溶液狀態的情況時,固形物濃度(組成物溶液中所占的溶劑以外的成分)可根據使用目的或所期望的膜厚的值等而設定為任意濃度(例如5質量%~50質量%)。作為更優選的固形物濃度,因於基板上形成塗膜的形成方法而異,於後文對其加以敍述。關於如此而調製的組成物溶液,可使用孔徑為0.5 μm左右的微孔過濾器等而進行過濾後,供至使用。 When the radiation sensitive resin composition is prepared in a solution state, the solid content concentration (component other than the solvent in the composition solution) can be set to any concentration depending on the purpose of use, the value of the desired film thickness, or the like. (for example, 5 mass% to 50 mass%). The more preferable solid content concentration differs depending on the method of forming the coating film on the substrate, which will be described later. The composition solution prepared in this manner can be filtered by using a micropore filter having a pore diameter of about 0.5 μm, and then used.
以上成分與調製方法的感放射線性樹脂組成物可利用低溫硬化而形成保護膜。具體而言,即使是在200℃以下的硬化溫度下、進一步而言為180℃以下的硬化溫度 下,亦可獲得具有良好的可靠性的保護膜。而且,可利用低溫硬化而提供本實施形態的彩色濾光片。 The radiation sensitive resin composition of the above components and the preparation method can be cured by low temperature to form a protective film. Specifically, even at a curing temperature of 200 ° C or lower, further, a curing temperature of 180 ° C or lower A protective film with good reliability can also be obtained. Further, the color filter of the present embodiment can be provided by low-temperature curing.
其次,對本實施形態的彩色濾光片的ITO電極加以說明。本實施形態的彩色濾光片在保護膜上具有ITO電極。ITO電極是使用濺射法等公知方法而在保護膜上形成ITO膜而形成的。另外,著色圖案上的透明電極除了ITO以外,可使用對可見光而言具有高的透射率與導電性的透明材料而構成。例如可使用氧化銦鋅(Indium Zinc Oxide,IZO)或ZnO(氧化鋅)等而構成。 Next, the ITO electrode of the color filter of the present embodiment will be described. The color filter of this embodiment has an ITO electrode on the protective film. The ITO electrode is formed by forming an ITO film on a protective film by a known method such as sputtering. Further, the transparent electrode on the colored pattern may be formed of a transparent material having high transmittance and conductivity for visible light, in addition to ITO. For example, indium zinc oxide (IZO), ZnO (zinc oxide), or the like can be used.
而且,本實施形態的彩色濾光片可以如上所述那樣在構成液晶顯示元件時的液晶層側的面上具有液晶配向控制用配向膜。亦即,於彩色濾光片的保護膜上的ITO電極上設有配向膜。本實施形態的彩色濾光片的配向膜是包含化學性穩定且耐熱性優異的聚醯亞胺的配向膜。而且實施了光分解型光配向技術的配向處理而賦予其液晶配向控制能力。光分解型光配向技術是對配向膜照射偏光的紫外線,於配向膜中各向異性地產生光分解反應,於配向膜中導入各向異性。而且,於本實施形態的彩色濾光片的配向膜中,聚醯亞胺選擇低極性結構者。配向膜是使用液晶配向劑而形成於彩色濾光片上。其次,對本實施形態的彩色濾光片的配向膜與形成該配向膜的本實施形態的液晶配向劑加以說明。 Further, the color filter of the present embodiment may have a liquid crystal alignment control alignment film on the liquid crystal layer side surface when the liquid crystal display element is formed as described above. That is, an alignment film is provided on the ITO electrode on the protective film of the color filter. The alignment film of the color filter of the present embodiment is an alignment film containing a polyimide which is chemically stable and excellent in heat resistance. Further, the alignment treatment of the photodegradable photoalignment technique is carried out to impart liquid crystal alignment control capability. The photodegradable photoalignment technique is an ultraviolet ray that irradiates a polarizing film to a aligning film, and anisotropically generates a photodecomposition reaction in the alignment film, and introduces anisotropy into the alignment film. Further, in the alignment film of the color filter of the present embodiment, the polyimine is selected to have a low polarity structure. The alignment film is formed on the color filter using a liquid crystal alignment agent. Next, the alignment film of the color filter of the present embodiment and the liquid crystal alignment agent of this embodiment which forms the alignment film will be described.
本實施形態的彩色濾光片的配向膜是對含有通式[a] 所表示的結構單元的聚醯亞胺膜照射偏光的紫外線而形成的。 The alignment film of the color filter of the present embodiment contains a general formula [a] The polyimine film of the structural unit shown is formed by irradiating polarized ultraviolet rays.
上述通式[a]中,P1表示具有脂環族結構的4價有機基,P2表示2價有機基。 In the above formula [a], P 1 represents a tetravalent organic group having an alicyclic structure, and P 2 represents a divalent organic group.
本實施形態的彩色濾光片的配向膜由於通式[a]的P1具有脂環族結構而實現低極性結構。 The alignment film of the color filter of the present embodiment has a low-polar structure because P 1 of the general formula [a] has an alicyclic structure.
含有上述通式[a]所表示的結構單元的聚醯亞胺膜可通過對聚醯胺酸(所述聚醯胺酸是使脂環族四羧酸二酐與下述式[b]所表示的二胺反應而獲得)進行脫水閉環而獲得。 The polyimine film containing the structural unit represented by the above formula [a] can be obtained by polyphosphonic acid (the polyamino acid is an alicyclic tetracarboxylic dianhydride and the following formula [b] The obtained diamine reaction is obtained by performing a dehydration ring closure.
[化31]H2N-P2-NH2 〔b〕 [Formula 31] H 2 NP 2 -NH 2 [b]
可於形成含有通式[a]所表示的結構單元的聚醯亞胺的膜時使用的脂環族四羧酸二酐例如可列舉:1,2,3,4-環丁烷四甲酸二酐、1,2,3,4-環戊烷四甲酸二酐、2,3,4,5-四氫呋 喃四甲酸二酐、1,2,4,5-環己烷四甲酸二酐、2,3,5-三羧基環戊基乙酸二酐、1,3,3a,4,5,9b-六氫-5-(四氫-2,5-二氧代-3-呋喃基)-萘並[1,2-c]呋喃-1,3-二酮、1,3,3a,4,5,9b-六氫-8-甲基-5-(四氫-2,5-二氧代-3-呋喃基)-萘並[1,2-c]呋喃-1,3-二酮、3-氧雜雙環[3.2.1]辛烷-2,4-二酮-6-螺-3'-(四氫呋喃-2',5'-二酮)、5-(2,5-二氧代四氫-3-呋喃基)-3-甲基-3-環己烯-1,2-二甲酸酐、3,5,6-三羧基-2-羧基甲基降冰片烷-2:3,5:6-二酐、2,4,6,8-四羧基雙環[3.3.0]辛烷-2:4,6:8-二酐、4,9-二氧雜三環[5.3.1.02,6]十一烷-3,5,8,10-四酮等。另外,於形成含有通式[a]所表示的結構單元的聚醯亞胺的膜時,亦可將該些四羧酸及其衍生物的1種或2種以上加以混合而使用。而且,如果是所得的聚醯亞胺受到紫外線照射而實現液晶配向控制能力的範圍,則亦可併用脂環族以外的其他四羧酸二酐。 The alicyclic tetracarboxylic dianhydride which can be used in the formation of the film of the polythenimine containing the structural unit represented by the general formula [a] is exemplified by 1,2,3,4-cyclobutanetetracarboxylic acid Anhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 2,3,4,5-tetrahydrofuran tetracarboxylic dianhydride, 1,2,4,5-cyclohexanetetracarboxylic dianhydride, 2, 3,5-tricarboxycyclopentyl acetic acid dianhydride, 1,3,3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphtho [1,2-c]furan-1,3-dione, 1,3,3a,4,5,9b-hexahydro-8-methyl-5-(tetrahydro-2,5-dioxo- 3-furyl)-naphtho[1,2-c]furan-1,3-dione, 3-oxabicyclo[3.2.1]octane-2,4-dione-6-spiro-3'-(tetrahydrofuran-2',5'-dione), 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dimethyl Anhydride, 3,5,6-tricarboxy-2-carboxymethylnorbornane-2:3,5:6-dianhydride, 2,4,6,8-tetracarboxybicyclo[3.3.0]octane- 2:4,6:8-dianhydride, 4,9-dioxatricyclo[5.3.1.0 2,6 ]undecane-3,5,8,10-tetraketone, and the like. In addition, when a film of a polyimine containing a structural unit represented by the general formula [a] is formed, one or two or more kinds of these tetracarboxylic acids and derivatives thereof may be used in combination. Further, if the obtained polyimine is subjected to ultraviolet irradiation to achieve a liquid crystal alignment control ability, other tetracarboxylic dianhydrides other than the alicyclic group may be used in combination.
本實施形態的彩色濾光片的配向膜具有低極性結構,且作為液晶顯示元件的配向膜而要求具備耐熱性與化學穩定性。為了實現此種性能,理想的是通式[a]的P1為選自由下述結構所構成的群組的至少1種結構。 The alignment film of the color filter of the present embodiment has a low polarity structure, and is required to have heat resistance and chemical stability as an alignment film of a liquid crystal display element. In order to achieve such a performance, it is preferable that P 1 of the general formula [a] is at least one structure selected from the group consisting of the following structures.
此處,於上述式中,P3、P4、P5及P6分別獨立地表示氫或碳數為1~4的有機基。 Here, in the above formula, P 3 , P 4 , P 5 and P 6 each independently represent hydrogen or an organic group having 1 to 4 carbon atoms.
作為可於形成含有上述通式[a]所表示的結構單元的聚醯亞胺的膜時使用的上述式[b]所表示的二胺,例如可列舉脂肪族二胺、脂環族二胺、芳香族二胺、二胺基有機矽氧烷等。 The diamine represented by the above formula [b] which can be used for forming a film of the polyimine which is a structural unit represented by the above-mentioned general formula [a], for example, an aliphatic diamine or an alicyclic diamine , an aromatic diamine, a diamine organic decane, and the like.
作為該些的具體例,脂肪族二胺例如可列舉1,3-間苯二甲胺、1,3-丙二胺、丁二胺、戊二胺、己二胺等;脂環族二胺例如可列舉1,4-二胺基環己烷、4,4'-亞甲基雙(環己胺)、1,3-雙(胺基甲基)環己烷等;芳香族二胺例如可列舉對苯二胺、4,4'-二胺基二苯基甲烷、4,4'-二胺基二苯硫醚、1,5-二胺基萘、2,2'-二甲基-4,4'-二胺基聯苯、4,4'-二胺基-2,2'-雙(三氟甲基)聯苯、2,7-二胺基茀、4,4'-二胺基二苯基醚、2,2-雙[4-(4-胺基苯氧基)苯基]丙烷、9,9-雙(4-胺基苯基)茀、2,2-雙[4-(4-胺基苯氧基)苯基]六氟丙烷、2,2-雙(4-胺基苯基)六氟丙烷、4,4'-(對伸苯基二異亞丙基)雙苯胺、4,4'-(間伸苯基二異亞丙基)雙苯胺、1,4-雙(4-胺基苯氧基)苯、4,4'-雙(4-胺基苯氧基)聯苯、2,6-二胺基吡啶、3,4-二胺基吡啶、2,4-二胺基嘧啶、3,6-二胺基吖啶、3,6-二胺基哢唑、N-甲基-3,6-二胺基哢唑、N-乙基-3,6-二胺基哢唑、N-苯基-3,6-二胺基哢唑、N,N'-雙(4-胺基苯基)-聯苯胺、N,N'-雙(4-胺基苯基)-N,N'-二甲基聯苯胺、十二烷氧基-2,4-二胺基苯、十五烷氧基-2,4-二胺基苯、十六烷氧基-2,4-二胺基苯、十八烷氧基-2,4-二胺基苯、十二烷 氧基-2,5-二胺基苯、十五烷氧基-2,5-二胺基苯、十六烷氧基-2,5-二胺基苯、十八烷氧基-2,5-二胺基苯、膽甾烷基氧基-3,5-二胺基苯、膽甾烯基氧基-3,5-二胺基苯、膽甾烷基氧基-2,4-二胺基苯、膽甾烯基氧基-2,4-二胺基苯、膽甾烷基3,5-二胺基苯甲酸酯、膽甾烯基3,5-二胺基苯甲酸酯、羊毛甾烷基3,5-二胺基苯甲酸酯、2,5-二胺基苯甲酸、3,5-二胺基苯甲酸、1,4-雙-(4-胺基苯基)-呱嗪等;二胺基有機矽氧烷例如可列舉1,3-雙(3-胺基丙基)-四甲基二矽氧烷等,除此以外亦可使用日本專利特開2010-97188號公報中所記載的二胺。 Specific examples of the aliphatic diamine include 1,3-m-xylylenediamine, 1,3-propanediamine, butanediamine, pentanediamine, hexamethylenediamine, and the like; alicyclic diamines. Examples thereof include 1,4-diaminocyclohexane, 4,4'-methylenebis(cyclohexylamine), 1,3-bis(aminomethyl)cyclohexane, and the like; and aromatic diamines such as Examples thereof include p-phenylenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfide, 1,5-diaminonaphthalene, 2,2'-dimethyl -4,4'-diaminobiphenyl, 4,4'-diamino-2,2'-bis(trifluoromethyl)biphenyl, 2,7-diaminopurine, 4,4'- Diaminodiphenyl ether, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 9,9-bis(4-aminophenyl)anthracene, 2,2-double [4-(4-Aminophenoxy)phenyl]hexafluoropropane, 2,2-bis(4-aminophenyl)hexafluoropropane, 4,4'-(p-phenylene diisopropylidene Diphenylamine, 4,4'-(m-phenylene diisopropylidene)diphenylamine, 1,4-bis(4-aminophenoxy)benzene, 4,4'-bis(4-amine Phenyloxy)biphenyl, 2,6-diaminopyridine, 3,4-diaminopyridine, 2,4-diaminopyrimidine, 3,6-diaminoacridine, 3,6-di Amino oxazole, N-methyl-3,6-diaminocarbazole, N-ethyl-3,6-diamino Oxazole, N-phenyl-3,6-diaminocarbazole, N,N'-bis(4-aminophenyl)-benzidine, N,N'-bis(4-aminophenyl)- N,N'-dimethylbenzidine, dodecyloxy-2,4-diaminobenzene, pentadecyloxy-2,4-diaminobenzene, hexadecyloxy-2,4 -diaminobenzene, octadecyloxy-2,4-diaminobenzene, dodecane Oxy-2,5-diaminobenzene, pentadecyloxy-2,5-diaminobenzene, cetyloxy-2,5-diaminobenzene, octadecyloxy-2, 5-diaminobenzene, cholestyloxy-3,5-diaminobenzene, cholestyloxy-3,5-diaminobenzene, cholesteryl-2,4- Diaminobenzene, cholestyloxy-2,4-diaminobenzene, cholesteryl 3,5-diaminobenzoate, cholesteryl 3,5-diaminobenzoic acid Acid ester, lanolin alkyl 3,5-diaminobenzoic acid ester, 2,5-diaminobenzoic acid, 3,5-diaminobenzoic acid, 1,4-bis-(4-amino group Phenyl)-pyridazine or the like; and examples of the diamine-based organodecane may, for example, be 1,3-bis(3-aminopropyl)-tetramethyldioxane, and other Japanese patents may be used. The diamine described in Japanese Laid-Open Patent Publication No. 2010-97188.
作為形成含有通式[a]所表示的結構單元的聚醯亞胺時所使用的聚醯胺酸的合成反應,優選相對於上述式[b]所表示的二胺的胺基1當量而言,脂環族四羧酸二酐的酸酐基成為0.2當量~2當量的比例,更優選成為0.3當量~1.2當量的比例。 The synthesis reaction of the polyaminic acid used in the formation of the polyimine containing the structural unit represented by the general formula [a] is preferably 1 equivalent of the amine group of the diamine represented by the above formula [b]. The acid anhydride group of the alicyclic tetracarboxylic dianhydride is in a ratio of 0.2 equivalent to 2 equivalents, more preferably in a ratio of 0.3 equivalent to 1.2 equivalents.
作為聚醯胺酸的合成反應,優選於有機溶劑中,於優選為-20℃~150℃、更優選為0℃~100℃的聚合溫度下,以優選為0.1小時~24小時、更優選為0.5小時~12小時的聚合時間而進行。 The synthesis reaction of polylysine is preferably carried out in an organic solvent at a polymerization temperature of preferably -20 ° C to 150 ° C, more preferably 0 ° C to 100 ° C, preferably 0.1 to 24 hours, more preferably It is carried out at a polymerization time of 0.5 to 12 hours.
此處,有機溶劑例如可列舉非質子性極性溶劑、酚及其衍生物、醇、酮、酯、醚、鹵代烴、烴等。 Here, examples of the organic solvent include an aprotic polar solvent, a phenol and a derivative thereof, an alcohol, a ketone, an ester, an ether, a halogenated hydrocarbon, a hydrocarbon, and the like.
作為該些有機溶劑的具體例,上述非質子性極性溶劑例如可列舉N-甲基-2-吡咯烷酮、N,N-二甲基乙醯胺、N,N-二甲基甲醯胺、二甲基亞碸、γ-丁內酯、四甲基脲、六甲 基磷醯三胺等;上述酚衍生物例如可列舉間甲酚、二甲苯酚、鹵代酚等;上述醇例如可列舉甲醇、乙醇、異丙醇、環己醇、乙二醇、丙二醇、1,4-丁二醇、三乙二醇、乙二醇單甲醚等;上述酮例如可列舉丙酮、丁酮、甲基異丁基酮、環己酮等;上述酯例如可列舉乳酸乙酯、乳酸丁酯、乙酸甲酯、乙酸乙酯、乙酸丁酯、甲氧基丙酸甲酯、乙氧基丙酸乙酯、草酸二乙酯、丙二酸二乙酯等;上述醚例如可列舉二乙醚、乙二醇甲醚、乙二醇乙醚、乙二醇正丙醚、乙二醇異丙醚、乙二醇正丁醚、乙二醇二甲醚、乙二醇乙醚乙酸酯、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇單甲醚乙酸酯、二乙二醇單乙醚乙酸酯、四氫呋喃等;上述鹵代烴例如可列舉二氯甲烷、1,2-二氯乙烷、1,4-二氯丁烷、三氯乙烷、氯苯、鄰二氯苯等;上述烴例如可列舉己烷、庚烷、辛烷、苯、甲苯、二甲苯、丙酸異戊酯、異丁酸異戊酯、二異戊醚等。 Specific examples of the organic solvent include, for example, N-methyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide, and the like. Methyl hydrazine, γ-butyrolactone, tetramethylurea, hexa Examples of the phenol derivative include m-cresol, xylenol, and halogenated phenol; and examples of the alcohol include methanol, ethanol, isopropanol, cyclohexanol, ethylene glycol, and propylene glycol. Examples of the ketone include 1,4-butanediol, triethylene glycol, and ethylene glycol monomethyl ether; and examples of the ketone include acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; and the above esters include, for example, lactic acid B. Ester, butyl lactate, methyl acetate, ethyl acetate, butyl acetate, methyl methoxypropionate, ethyl ethoxypropionate, diethyl oxalate, diethyl malonate, etc.; Examples thereof include diethyl ether, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol n-propyl ether, ethylene glycol isopropyl ether, ethylene glycol n-butyl ether, ethylene glycol dimethyl ether, ethylene glycol ethyl ether acetate, Diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate And tetrahydrofuran or the like; examples of the halogenated hydrocarbon include dichloromethane, 1,2-dichloroethane, 1,4-dichlorobutane, trichloroethane, chlorobenzene, o-dichlorobenzene, and the like; Include hydrocarbons such as hexane, heptane, octane, benzene, toluene, xylene, isoamyl propionate, isoamyl isobutyrate, diisoamyl ether and the like.
於該些有機溶劑中,優選使用選自由非質子性極性溶劑以及酚及其衍生物所構成的群組(第一群組的有機溶劑)的一種以上、或者選自第一群組的有機溶劑的一種以上與選自由醇、酮、酯、醚、鹵代烴及烴所構成的群組(第二群組的有機溶劑)的一種以上的混合物。於後者的情況下, 作為第二群組的有機溶劑的使用比例,相對於第一群組的有機溶劑及第二群組的有機溶劑的合計而言優選為50 wt%以下,更優選為40 wt%以下,進一步更優選為30 wt%以下。 Among the organic solvents, it is preferred to use one or more selected from the group consisting of an aprotic polar solvent and a phenol and a derivative thereof (the first group of organic solvents), or an organic solvent selected from the first group. One or more kinds of a mixture of one or more selected from the group consisting of alcohols, ketones, esters, ethers, halogenated hydrocarbons, and hydrocarbons (the second group of organic solvents). In the latter case, The use ratio of the organic solvent as the second group is preferably 50% by weight or less, more preferably 40% by weight or less, based on the total of the organic solvent of the first group and the organic solvent of the second group, and further It is preferably 30 wt% or less.
有機溶劑的使用量(a)優選設為如下的量:脂環族四羧酸二酐及二胺的合計量(t)相對於反應溶液的總量(s+t)而言成為0.1 wt%~50 wt%的量。 The amount (a) of the organic solvent to be used is preferably an amount in which the total amount (t) of the alicyclic tetracarboxylic dianhydride and the diamine becomes 0.1 wt% with respect to the total amount (s+t) of the reaction solution. ~50 wt% amount.
如上所述而獲得使聚醯胺酸溶解而成的反應溶液。 A reaction solution obtained by dissolving polylysine was obtained as described above.
該反應溶液可直接供至液晶配向劑的調製,也可以使反應溶液中所含的聚醯胺酸離析後供至液晶配向劑的調製,或者對離析的聚醯胺酸進行純化後供至液晶配向劑的調製。 The reaction solution may be directly supplied to the liquid crystal alignment agent, or may be prepared by isolating the polylysine contained in the reaction solution to the liquid crystal alignment agent, or purifying the isolated polyamic acid to the liquid crystal. Modulation of the alignment agent.
於使聚醯胺酸進行脫水閉環而製成聚醯亞胺的情況時,可將上述反應溶液直接供至脫水閉環反應,亦可將反應溶液中所含的聚醯胺酸離析後供至脫水閉環反應,或者對離析的聚醯胺酸進行純化後供至脫水閉環反應。聚醯胺酸的離析及純化可依照公知的方法而進行。 When polylysine is subjected to dehydration ring closure to form a polyimine, the reaction solution may be directly supplied to a dehydration ring-closure reaction, or the polylysine contained in the reaction solution may be isolated and dehydrated. The ring closure reaction, or the isolated polylysine is purified and supplied to the dehydration ring closure reaction. The isolation and purification of polylysine can be carried out in accordance with a known method.
含有上述通式[a]所表示的結構單元的聚醯亞胺可通過如下方式而獲得:對如上所述地合成的聚醯胺酸進行脫水閉環而醯亞胺化。 The polyimine containing the structural unit represented by the above formula [a] can be obtained by subjecting the polylysine synthesized as described above to dehydration ring closure to ruthenium.
構成本實施形態的彩色濾光片的配向膜的聚醯亞胺可為作為其前驅物的聚醯胺酸所具有的醯胺酸結構全部脫水閉環而成的完全醯亞胺化物,亦可為醯胺酸結構的僅僅一部分脫水閉環,醯胺酸結構與醯亞胺環結構並存的部分 醯亞胺化物。作為構成本實施形態的彩色濾光片的配向膜的聚醯亞胺,其醯亞胺化率優選為30%以上,更優選為50%~100%,更優選為65%~100%。該醯亞胺化率是以百分率表示醯亞胺環結構數相對於聚醯亞胺的醯胺酸結構數與醯亞胺環結構數的合計所占的比例。此處,醯亞胺環的一部分亦可為異醯亞胺環。 The polyimine of the alignment film constituting the color filter of the present embodiment may be a fully ruthenium imide formed by dehydration ring closure of a proline structure of polyglycine as a precursor thereof, or may be Only a part of the structure of the proline is dehydrated and closed, and the part of the proline structure and the quinone ring structure coexist. Yttrium imide. The polyimine which constitutes the alignment film of the color filter of the present embodiment preferably has a ruthenium iodide ratio of 30% or more, more preferably 50% to 100%, and still more preferably 65% to 100%. The ruthenium imidization ratio is a ratio of the number of quinone ring structures to the total number of guanidine structures and the number of quinone ring structures of the polyimine. Here, a part of the quinone ring may also be an isoindole ring.
聚醯胺酸的脫水閉環優選通過如下方法而進行:對聚醯胺酸進行加熱的方法;或者將聚醯胺酸溶解於有機溶劑中,於該溶液中添加脫水劑及脫水閉環催化劑而視需要進行加熱的方法。其中優選利用後者的方法。 The dehydration ring closure of polylysine is preferably carried out by a method of heating polylysine; or dissolving polylysine in an organic solvent, adding a dehydrating agent and a dehydration ring-closing catalyst to the solution, as needed The method of heating. Among them, the latter method is preferably used.
於上述聚醯胺酸溶液中添加脫水劑及脫水閉環催化劑的方法中,脫水劑例如可使用乙酸酐、丙酸酐、三氟乙酸酐等酸酐。作為脫水劑的使用量,相對於聚醯胺酸的醯胺酸結構1莫耳而言優選為0.01莫耳~20莫耳。脫水閉環催化劑例如可使用吡啶、三甲吡啶、二甲吡啶、三乙胺等三級胺。作為脫水閉環催化劑的使用量,相對於所使用的脫水劑1莫耳而言優選為0.01莫耳~10莫耳。作為脫水閉環反應中所使用的有機溶劑,可列舉作為聚醯胺酸的合成中所使用的有機溶劑而例示的有機溶劑。脫水閉環反應的反應溫度優選為0℃~180℃,更優選為10℃~150℃。反應時間優選為1.0小時~120小時,更優選為2.0小時~30小時。 In the method of adding a dehydrating agent and a dehydration ring-closure catalyst to the above polyamic acid solution, an acid anhydride such as acetic anhydride, propionic anhydride or trifluoroacetic anhydride can be used as the dehydrating agent. The amount of the dehydrating agent to be used is preferably 0.01 mol to 20 mol with respect to the proline structure of polylysine. As the dehydration ring-closing catalyst, for example, a tertiary amine such as pyridine, trimethylpyridine, dimethylpyridine or triethylamine can be used. The amount of use as the dehydration ring-closure catalyst is preferably 0.01 mol to 10 mol per mol of the dehydrating agent used. The organic solvent used for the dehydration ring-closure reaction is exemplified as an organic solvent exemplified as the organic solvent used in the synthesis of polyglycine. The reaction temperature of the dehydration ring closure reaction is preferably from 0 ° C to 180 ° C, more preferably from 10 ° C to 150 ° C. The reaction time is preferably from 1.0 to 120 hours, more preferably from 2.0 to 30 hours.
如此進行而獲得含有聚醯亞胺的反應溶液。該反應溶液可直接供至液晶配向劑的調製,也可以自反應溶液中除 去脫水劑及脫水閉環催化劑後而供至液晶配向劑的調製,也可以使聚醯亞胺離析後而供至液晶配向劑的調製,或者也可以對離析的聚醯亞胺進行純化後供至液晶配向劑的調製。該些純化操作可依照公知的方法而進行。 This was carried out to obtain a reaction solution containing polyimine. The reaction solution can be directly supplied to the preparation of the liquid crystal alignment agent, or can be removed from the reaction solution. After dehydrating agent and dehydration ring-closing catalyst are supplied to the liquid crystal alignment agent, the polyimine may be isolated and supplied to the liquid crystal alignment agent, or the isolated polyimine may be purified and then supplied. Modulation of liquid crystal alignment agent. These purification operations can be carried out in accordance with a known method.
本實施形態的液晶配向劑是使上述的聚醯胺酸或使用該聚醯胺酸而所得的含有上述通式[a]所表示的結構單元的聚醯亞胺、及視需要而任意調配的其他成分優選溶解含有有機溶劑中而構成。其他成分例如可列舉上述聚醯胺酸及由該聚醯胺酸而所得的含有上述通式[a]所表示的結構單元的聚醯亞胺以外的聚合物、硬化劑、硬化催化劑、硬化促進劑、環氧化合物、官能性矽烷化合物、界面活性劑、光敏劑等。 In the liquid crystal alignment agent of the present embodiment, the above-mentioned polyaminic acid or a polyimine containing the structural unit represented by the above formula [a] obtained by using the polyamic acid, and optionally arbitrarily formulated The other components are preferably dissolved in an organic solvent. The other component is, for example, a polymer other than the polyaminic acid and the polyimine containing the structural unit represented by the above formula [a], a curing agent, a curing catalyst, and a curing accelerator. Agents, epoxy compounds, functional decane compounds, surfactants, photosensitizers, and the like.
本實施形態的液晶配向劑中所使用的有機溶劑例如可列舉N-甲基-2-吡咯烷酮、γ-丁內酯、γ-丁內醯胺、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、4-羥基-4-甲基-2-戊酮、乙二醇單甲醚、乳酸丁酯、乙酸丁酯、甲氧基丙酸甲酯、乙氧基丙酸乙酯、乙二醇甲醚、乙二醇乙醚、乙二醇正丙醚、乙二醇異丙醚、乙二醇正丁醚(丁基溶纖劑)、乙二醇二甲醚、乙二醇乙醚乙酸酯、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇單甲醚乙酸酯、二乙二醇單乙醚乙酸酯、二異丁酮、丙酸異戊酯、異丁酸異戊酯、二異戊醚、碳酸乙二酯、碳酸丙二酯等。該些有機溶劑可單獨使用或者將2種以上混合使用。 Examples of the organic solvent used in the liquid crystal alignment agent of the present embodiment include N-methyl-2-pyrrolidone, γ-butyrolactone, γ-butylide, N,N-dimethylformamide, and N. , N-dimethylacetamide, 4-hydroxy-4-methyl-2-pentanone, ethylene glycol monomethyl ether, butyl lactate, butyl acetate, methyl methoxypropionate, ethoxylate Ethyl propionate, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol n-propyl ether, ethylene glycol isopropyl ether, ethylene glycol n-butyl ether (butyl cellosolve), ethylene glycol dimethyl ether, ethylene glycol Ethyl acetate, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether acetate, diethylene glycol Monoethyl ether acetate, diisobutyl ketone, isoamyl propionate, isoamyl isobutyrate, diisoamyl ether, ethylene carbonate, propylene carbonate, and the like. These organic solvents may be used singly or in combination of two or more.
本發明的液晶配向劑中的固形物濃度(液晶配向劑中的除溶劑以外的成分的合計重量於液晶配向劑的總重量中所占的比例)可考慮黏性、揮發性等而適宜選擇,優選為1 wt%~10 wt%的範圍。亦即,本發明的液晶配向劑可如後所述那樣塗布於基板表面上,優選進行加熱而形成作為液晶配向膜的塗膜或成為液晶配向膜的塗膜,但於固形物濃度不足1 wt%時,該塗膜的膜厚變得過小而無法獲得良好的液晶配向膜;另一方面,若固形物濃度超過10 wt%時,塗膜的膜厚變得過大而無法獲得良好的液晶配向膜,而且,液晶配向劑的黏性增大而造成塗布特性變差。 The solid content concentration in the liquid crystal alignment agent of the present invention (the ratio of the total weight of components other than the solvent in the liquid crystal alignment agent to the total weight of the liquid crystal alignment agent) can be appropriately selected in consideration of viscosity, volatility, and the like. It is preferably in the range of 1 wt% to 10 wt%. In other words, the liquid crystal alignment agent of the present invention can be applied to the surface of the substrate as described later, and is preferably heated to form a coating film as a liquid crystal alignment film or a coating film to be a liquid crystal alignment film, but the solid concentration is less than 1 wt. In the case of %, the film thickness of the coating film is too small to obtain a good liquid crystal alignment film; on the other hand, when the solid content exceeds 10 wt%, the film thickness of the coating film becomes too large to obtain a good liquid crystal alignment. Further, the film and the viscosity of the liquid crystal alignment agent are increased to cause deterioration in coating properties.
特別優選的固形物濃度的範圍因將液晶配向劑塗布於基板上時所使用的方法而異。例如,於利用旋轉器法(旋轉塗布法)的情況時,特別優選固形物濃度為1.5 wt%~4.5 wt%的範圍。於利用印刷法的情況時,特別優選使固形物濃度為3 wt%~9 wt%的範圍,由此而使溶液黏度成為12 mPa.s~50 mPa.s的範圍。於利用噴墨法的情況時,特別優選使固形物濃度為1 wt%~5 wt%的範圍,由此而使溶液黏度成為3 mPa.s~15 mPa.s的範圍。 A particularly preferable range of the solid content concentration varies depending on the method used when the liquid crystal alignment agent is applied onto the substrate. For example, in the case of using the rotator method (rotary coating method), the solid content concentration is particularly preferably in the range of 1.5 wt% to 4.5 wt%. In the case of using the printing method, it is particularly preferable to make the solid content concentration in the range of 3 wt% to 9 wt%, thereby making the solution viscosity 12 mPa. s~50 mPa. The scope of s. In the case of using the ink jet method, it is particularly preferable to make the solid content concentration in the range of 1 wt% to 5 wt%, thereby making the solution viscosity 3 mPa. s~15 mPa. The scope of s.
使用旋轉器法、轉印印刷法、噴墨法等方法而將如上所述而所得的本實施形態的聚醯亞胺或聚醯胺酸溶液塗布於基板上,對其進行加熱硬化而形成聚醯亞胺膜。此時的硬化溫度優選選擇可抑制著色圖案褪色的溫度,理想的是150℃以上200℃以下,更優選為150℃以上180℃以下。聚醯亞胺膜的厚度並無特別限定,考慮作為液晶配向膜而 使用,則優選為0.001 μm~1 μm,更優選為0.005 μm~0.5 μm,進一步更優選為0.01 μm~0.3 μm。 The polyimine or polylysine solution of the present embodiment obtained as described above is applied onto a substrate by a method such as a spinner method, a transfer printing method, or an inkjet method, and is heated and cured to form a poly醯 imine film. The curing temperature at this time is preferably selected to suppress the fading of the colored pattern, and is preferably 150° C. or higher and 200° C. or lower, and more preferably 150° C. or higher and 180° C. or lower. The thickness of the polyimide film is not particularly limited, and it is considered as a liquid crystal alignment film. The use is preferably 0.001 μm to 1 μm, more preferably 0.005 μm to 0.5 μm, still more preferably 0.01 μm to 0.3 μm.
其次,通過於所形成的聚醯亞胺的膜表面照射直線偏光或部分偏光的放射線、或非偏光的放射線,而於聚醯亞胺的膜中導入各向異性,賦予液晶配向能力。如此的處理與摩擦處理等先前的配向處理的方法對應,可更簡便地進行。此處,放射線例如可使用包含100 nm~400 nm的波長光的紫外線。而且,優選根據所使用的聚醯亞胺的種類而經由濾波器等選擇適宜的波長,進行照射。當所使用的放射線為直線偏光或部分偏光的情況時,照射可自垂直於基板面的方向進行,也可以自斜方向進行以賦予預傾角,而且亦可將該些方法組合而進行。在照射非偏光的放射線的情況時,照射方向必需是斜方向。 Next, by irradiating a linearly polarized light or a partially polarized radiation or a non-polarized radiation on the surface of the formed polyimide film, anisotropy is introduced into the film of the polyimide, and the liquid crystal alignment ability is imparted. Such a process corresponds to the method of the previous alignment process, such as a rubbing process, and can be performed more easily. Here, as the radiation, for example, ultraviolet rays containing light having a wavelength of 100 nm to 400 nm can be used. Further, it is preferred to perform irradiation by selecting an appropriate wavelength via a filter or the like depending on the type of the polyimide. When the radiation to be used is linearly polarized or partially polarized, the irradiation may be performed from a direction perpendicular to the substrate surface, or may be performed from an oblique direction to impart a pretilt angle, or may be performed by combining the methods. In the case of irradiating non-polarized radiation, the irradiation direction must be an oblique direction.
紫外線的照射時間優選為數秒至數小時的範圍,優選根據所使用的聚醯亞胺的種類而選擇適宜的時間。 The irradiation time of the ultraviolet rays is preferably in the range of several seconds to several hours, and it is preferred to select an appropriate time depending on the type of the polyimide used.
以上,對構成本實施形態的彩色濾光片的各構成構件進行了詳細說明,其次對本實施形態的彩色濾光片的製造方法加以說明。 The respective constituent members constituting the color filter of the present embodiment have been described in detail. Next, a method of manufacturing the color filter of the present embodiment will be described.
在本實施形態的彩色濾光片的製造中,包括用以由上述著色組成物而形成著色圖案的步驟、用以使用上述液晶配向劑而形成配向膜的步驟作為主要的製造步驟。而且,亦可於著色圖案上形成保護膜。在這種情況下,變得包含 由上述感放射線性樹脂組成物形成保護膜的步驟。以下,對彩色濾光片及該些的製造方法加以說明。 In the production of the color filter of the present embodiment, a step of forming a colored pattern from the colored composition and a step of forming an alignment film using the liquid crystal alignment agent are included as main manufacturing steps. Further, a protective film may be formed on the colored pattern. In this case, become included A step of forming a protective film from the above-described radiation sensitive resin composition. Hereinafter, a color filter and a method of manufacturing the same will be described.
本實施形態的彩色濾光片的製造方法至少以如下的順序包含下述步驟[1]~步驟[5]:[1]在基板上形成著色組成物塗膜的步驟(以下有時稱為“[1]步驟”)、[2]在著色組成物塗膜上形成著色圖案的步驟(以下有時稱為“[2]步驟”)、[3]在200℃以下對形成有著色圖案的塗膜進行硬化的步驟(以下有時稱為“[3]步驟”)、[4]在[3]步驟後的基板上形成聚醯亞胺膜的步驟(以下有時稱為“[4]步驟”)、[5]對聚醯亞胺膜照射偏光的紫外線而形成配向膜的步驟(以下有時稱為“[5]步驟”)。 The method for producing a color filter of the present embodiment includes the following steps [1] to [5] in the following order: [1] a step of forming a coating film for a colored composition on a substrate (hereinafter sometimes referred to as " [1] Steps "), [2] A step of forming a colored pattern on a colored composition coating film (hereinafter sometimes referred to as "[2] step"), [3] coating a colored pattern at 200 ° C or lower The step of hardening the film (hereinafter sometimes referred to as "[3] step"), [4] the step of forming a polyimide film on the substrate after the step [3] (hereinafter sometimes referred to as "[4] step) "), [5] A step of forming a alignment film by irradiating a polarized ultraviolet ray to a polyimide film (hereinafter sometimes referred to as "[5] step").
而且,本實施形態的彩色濾光片可於著色圖案上具有保護膜。在這種情況下,可以在上述[3]步驟與上述[4]步驟之間以如下順序而包含下述步驟[x]~步驟[xiii]:[x]於[3]步驟後的基板上形成感放射線性樹脂組成物塗膜的步驟(以下有時稱為“[x]步驟”)、[xi]對該基板上的感放射線性樹脂組成物塗膜的至少一部分照射放射線的步驟(以下有時稱為“[xi]步驟”)、[xii]對照射了放射線的塗膜進行顯影的步驟(以下有時稱為“[xii]步驟”)、[xiii]在200℃以下使進行了顯影的塗膜硬化的步驟 (以下有時稱為“[xiii]步驟”)。 Further, the color filter of the present embodiment can have a protective film on the colored pattern. In this case, the following steps [x] to [xiii] may be included between the above [3] step and the above [4] step in the following order: [x] on the substrate after the [3] step a step of forming a radiation-sensitive resin composition coating film (hereinafter sometimes referred to as "[x] step"), [xi] a step of irradiating at least a part of the radiation-sensitive resin composition coating film on the substrate (hereinafter, The step of developing the coating film irradiated with radiation (hereinafter sometimes referred to as "[xii] step") and [xiii] may be performed at 200 ° C or lower, sometimes referred to as "[xi] step"), [xii]. Developing film hardening step (The following is sometimes referred to as "[xiii] step").
通過以上的本實施形態的彩色濾光片的製造方法,可使用上述本實施形態的著色組成物而於基板上形成著色圖案,使用上述本實施形態的液晶配向劑而形成光配向技術的配向膜。而且,可使用上述本實施形態的感放射線性樹脂組成物而形成保護膜。其結果,可形成耐熱性、耐化學品性、電壓保持率等良好的彩色濾光片。在這種情況下,可實現低溫硬化,且於上述[3]步驟中,變得可於200℃以下的溫度下進行著色圖案的硬化。即使在著色圖案上形成保護膜的情況下,於上述[xiii]的硬化步驟中,變得可於200℃以下的溫度下進行保護膜的硬化。因此,可在上述著色組成物中使用在耐熱性方面存在課題的染料而作為著色劑。因此,利用本實施形態的彩色濾光片的製造方法,可製造顏色特性優異的彩色濾光片。 According to the method for producing a color filter of the present embodiment, the colored composition of the present embodiment can be used to form a colored pattern on the substrate, and the alignment film of the photoalignment technique can be formed by using the liquid crystal alignment agent of the present embodiment. . Further, the radiation-sensitive resin composition of the present embodiment described above can be used to form a protective film. As a result, a color filter excellent in heat resistance, chemical resistance, voltage holding ratio, and the like can be formed. In this case, low-temperature hardening can be achieved, and in the above step [3], the coloring pattern can be cured at a temperature of 200 ° C or lower. Even in the case where a protective film is formed on the colored pattern, in the hardening step of the above [xiii], the curing of the protective film can be performed at a temperature of 200 ° C or lower. Therefore, as the coloring agent, a dye having a problem in heat resistance can be used as the coloring composition. Therefore, according to the method for producing a color filter of the present embodiment, a color filter excellent in color characteristics can be produced.
另外,作為利用本實施形態的彩色濾光片的製造方法而製造的彩色濾光片,於自節能的觀點考慮而期望加熱步驟低溫化的情況下,亦成為適宜的彩色濾光片。 In addition, as a color filter manufactured by the method for producing a color filter of the present embodiment, when a heating step is desired to be lowered from the viewpoint of energy saving, it is also a suitable color filter.
以下,對本實施形態的彩色濾光片的製造方法中的各步驟加以詳述。 Hereinafter, each step in the method of manufacturing the color filter of the present embodiment will be described in detail.
在本步驟中,在基板上形成上述本實施形態的著色組成物的塗膜。 In this step, a coating film of the coloring composition of the above-described embodiment is formed on a substrate.
在基板表面上,視需要而以劃分形成像素的部分的方式形成遮光層(黑色矩陣)。其次,在該基板上塗布例如 含有紅色的[IV]著色劑的著色組成物,然後進行預焙而使溶劑蒸發,從而形成塗膜。另外,在基板上形成著色圖案的其他方法可採用日本專利特開平7-318723號公報及日本專利特開2000-310706號公報等中所揭示的利用噴墨方式而獲得各色像素的方法。該方法首先在基板表面上形成兼具遮光功能的隔板。其次,利用噴墨裝置將例如含有紅色著色劑的著色組成物噴出至所形成的隔板內,然後進行預焙而使溶劑蒸發。其次,視需要對該塗膜進行曝光而形成紅色的像素圖案。另外,上述隔板不僅僅起到遮光功能,而且發揮用以使噴出至劃區內的各色的著色組成物並不混色的功能,因此與上述黑色矩陣相比而言膜厚較厚。 On the surface of the substrate, a light shielding layer (black matrix) is formed in a manner to divide a portion where the pixels are formed as needed. Next, coating on the substrate, for example A colored composition containing a red [IV] colorant is then prebaked to evaporate the solvent to form a coating film. In addition, a method of obtaining a color pattern by using an inkjet method disclosed in Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. This method first forms a separator having a light-shielding function on the surface of the substrate. Next, a coloring composition containing, for example, a red coloring agent is ejected into the formed separator by an ink jet apparatus, and then prebaked to evaporate the solvent. Next, the coating film is exposed as needed to form a red pixel pattern. Further, the separator not only functions as a light-shielding function, but also functions to prevent the coloring composition of each color discharged into the scribe region from being mixed, and therefore has a thicker film thickness than the black matrix.
基板的材料例如可列舉鈉鈣玻璃或無鹼玻璃等玻璃、矽、聚對苯二甲酸乙二酯、聚對苯二甲酸丁二酯、聚醚碸、聚碳酸酯、芳香族聚醯胺、聚醯胺醯亞胺、聚醯亞胺等。而且,亦可視需要對該些基板預先實施利用矽烷偶聯劑等的藥劑處理、等離子體處理、離子鍍、濺射、氣相反應法、真空蒸鍍等適宜的預處理。 Examples of the material of the substrate include glass such as soda lime glass or alkali-free glass, bismuth, polyethylene terephthalate, polybutylene terephthalate, polyether oxime, polycarbonate, and aromatic polyamine. Polyamidomine, polyimine, and the like. Further, an appropriate pretreatment such as a chemical treatment such as a decane coupling agent, plasma treatment, ion plating, sputtering, gas phase reaction method, or vacuum vapor deposition may be previously performed on the substrates.
將著色組成物塗布於基板上的方法可列舉噴霧法、輥塗法、旋轉塗布法(有時亦稱為旋塗法或旋轉器法)、狹縫口模塗布法、棒式塗布法等。該些方法中優選旋塗法、狹縫口模塗布法。 Examples of the method of applying the colored composition to the substrate include a spray method, a roll coating method, a spin coating method (also sometimes referred to as a spin coating method or a spinner method), a slit die coating method, a bar coating method, and the like. Among these methods, a spin coating method or a slit die coating method is preferred.
預焙通常藉由將減壓乾燥與加熱乾燥組合而進行。減壓乾燥通常以到達50 Pa~200 Pa的方式進行。而且,加熱乾燥的條件通常是在70℃~110℃為1分鐘~10分鐘左 右。 Prebaking is usually carried out by combining reduced pressure drying with heat drying. Drying under reduced pressure is usually carried out in such a manner as to reach 50 Pa to 200 Pa. Moreover, the conditions of heat drying are usually from 1 minute to 10 minutes at 70 ° C to 110 ° C. right.
乾燥後的膜厚通常為0.6 μm~8.0 μm,優選為1.2 μm~5.0 μm。 The film thickness after drying is usually from 0.6 μm to 8.0 μm, preferably from 1.2 μm to 5.0 μm.
在[2]步驟中,介隔光掩模而對[1]步驟中所形成的塗膜進行曝光,使用鹼性顯影液而進行顯影,溶解除去塗膜的未曝光部分,藉此可獲得以規定的排列而配置有紅色的像素圖案的硬化前的著色圖案。 In the step [2], the coating film formed in the step [1] is exposed through a photomask, developed using an alkaline developing solution, and the unexposed portion of the coating film is dissolved and removed, whereby The coloring pattern before hardening of the red pixel pattern is arranged in a predetermined arrangement.
其次,使用綠色或藍色的各著色組成物,反覆進行上述[1]步驟及[2]步驟而在同一基板上依序形成綠色著色圖案及藍色著色圖案。由此而獲得在基板上配置有紅色、綠色及藍色的三原色的硬化前的著色圖案的彩色濾光片。其中,在本實施形態中,形成各色像素的順序及顏色數並不限定於上述順序及顏色數。 Next, using the green or blue colored composition, the above steps [1] and [2] are repeatedly performed to sequentially form a green colored pattern and a blue colored pattern on the same substrate. Thereby, a color filter in which the coloring patterns before curing of the three primary colors of red, green, and blue are disposed on the substrate is obtained. However, in the present embodiment, the order in which the pixels of the respective colors are formed and the number of colors are not limited to the above order and the number of colors.
而且,黑色矩陣可通過利用光刻法將通過濺鍍或蒸鍍而形成的鉻等的金屬薄膜製成所期望的圖案而形成,使用含有黑色著色劑的著色組成物而與上述像素的形成的情況同樣地形成。 Further, the black matrix can be formed by forming a metal film of chromium or the like formed by sputtering or vapor deposition into a desired pattern by photolithography, and forming a coloring composition containing a black colorant with the above-described pixel. The situation is similarly formed.
放射線的光源例如可列舉氙氣燈、鹵素燈、鎢絲燈、高壓水銀燈、超高壓水銀燈、金鹵燈、中壓水銀燈、低壓水銀燈等燈光源或氬離子激光器、YAG激光器、XeCl準分子激光器、氮激光器等激光光源等。優選波長處於190 nm~450 nm的範圍的放射線。放射線的曝光量優選為10 J/m2~10,000 J/m2。 Examples of the radiation source include a xenon lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, a medium pressure mercury lamp, a low pressure mercury lamp, or the like, or an argon ion laser, a YAG laser, a XeCl excimer laser, and a nitrogen gas. Laser light source such as a laser. Radiation having a wavelength in the range of 190 nm to 450 nm is preferred. The exposure amount of the radiation is preferably from 10 J/m 2 to 10,000 J/m 2 .
鹼性顯影液優選碳酸鈉、氫氧化鈉、氫氧化鉀、四甲基氫氧化銨、膽鹼、1,8-二氮雜雙環-[5.4.0]-7-十一碳烯、1,5-二氮雜雙環-[4.3.0]-5-壬烯。 The alkaline developing solution is preferably sodium carbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo-[5.4.0]-7-undecene, 1, 5-diazabicyclo-[4.3.0]-5-decene.
在鹼性顯影液中可適量添加例如甲醇、乙醇等水溶性有機溶劑或界面活性劑等。另外,在鹼顯影後通常進行水洗。顯影處理法可應用噴淋顯影法、噴射顯影法、浸漬(dip)顯影法、覆液(puddle)顯影法等。顯影條件優選在常溫下為5秒~300秒。 A water-soluble organic solvent such as methanol or ethanol or a surfactant may be added to the alkaline developer in an appropriate amount. Further, water washing is usually carried out after alkali development. As the development treatment method, a shower development method, a spray development method, a dip development method, a puddle development method, or the like can be applied. The developing conditions are preferably from 5 seconds to 300 seconds at normal temperature.
在[2]步驟中形成著色圖案後,可通過進行硬化(亦稱為後烘)而使著色圖案硬化,從而可使著色圖案的形成結束。後烘的加熱條件是200℃以下。後烘的加熱時間是10分鐘~60分鐘。在本實施形態中,即使後烘溫度為低溫,亦可獲得耐溶劑性等良好的著色圖案。具體而言,即使後烘溫度為200℃以下、進一步為180℃以下,亦可獲得具有充分的耐溶劑性等的彩色濾光片。像素的膜厚通常為0.5 μm~5.0 μm,優選為1.0 μm~3.0 μm。另外,為了使硬度等提高至實際上商業上所要求的水準,通常必需在超過120℃的溫度下的硬化步驟。而且,在180℃以下的範圍內,優選在更高溫度下的硬化。 After the coloring pattern is formed in the step [2], the colored pattern can be hardened by performing hardening (also referred to as post-baking), whereby the formation of the colored pattern can be completed. The heating condition for post-baking is 200 ° C or lower. The post-baking heating time is 10 minutes to 60 minutes. In the present embodiment, even if the post-baking temperature is low, a good coloring pattern such as solvent resistance can be obtained. Specifically, even if the post-baking temperature is 200° C. or lower and further 180° C. or lower, a color filter having sufficient solvent resistance or the like can be obtained. The film thickness of the pixel is usually from 0.5 μm to 5.0 μm, preferably from 1.0 μm to 3.0 μm. Further, in order to increase the hardness and the like to a level which is practically required in the art, a hardening step at a temperature exceeding 120 ° C is usually required. Moreover, in the range of 180 ° C or lower, hardening at a higher temperature is preferred.
而且,於本實施形態的彩色濾光片的製造中,於形成著色圖案後,具有形成ITO電極的步驟。形成ITO電極的方法可利用濺鍍法等,於著色圖案上形成包含ITO的透明導電層而進行。另外,於著色圖案上配置保護膜的情況時, 於後述的保護膜形成步驟後,於所形成的保護膜上形成透明導電層。其次,於必需圖案化的ITO電極時,通過利用光刻法而對該透明導電層進行蝕刻,可於著色圖案或保護膜上形成圖案化的透明ITO電極。 Further, in the production of the color filter of the present embodiment, after the coloring pattern is formed, there is a step of forming an ITO electrode. The method of forming the ITO electrode can be performed by forming a transparent conductive layer containing ITO on the colored pattern by a sputtering method or the like. Further, when a protective film is placed on the colored pattern, After the protective film forming step described later, a transparent conductive layer is formed on the formed protective film. Next, when the ITO electrode is required to be patterned, the transparent conductive layer is etched by photolithography to form a patterned transparent ITO electrode on the colored pattern or the protective film.
在[4]步驟中使用上述本實施形態的液晶配向劑。而且,在通過上述的[1]步驟~[3]步驟而形成有著色圖案的基板的ITO電極上,利用例如輥塗法、旋轉器法、印刷法、噴墨法等適宜的塗布方法而塗布液晶配向劑。其次,對塗布有液晶配向劑的基板進行預焙,其後進行後烘,由此而形成含有上述通式[a]所表示的結構單元的聚醯亞胺的塗膜。預焙條件例如是在40℃~120℃下進行0.1分鐘~5分鐘。後烘條件是在120℃~230℃、優選為150℃~200℃、更優選為150℃~180℃下進行5分鐘~200分鐘、優選為10分鐘~100分鐘。後烘後的塗膜的膜厚優選為0.001 μm~1 μm,更優選為0.005 μm~0.5 μm,進一步更優選為0.01 μm~0.3 μm。 The liquid crystal alignment agent of the above embodiment is used in the step [4]. Further, the ITO electrode on which the colored pattern is formed by the steps [1] to [3] described above is applied by a suitable coating method such as a roll coating method, a spinner method, a printing method, or an inkjet method. Liquid crystal alignment agent. Next, the substrate coated with the liquid crystal alignment agent is prebaked, and then post-baked to form a coating film of the polyimine containing the structural unit represented by the above formula [a]. The prebaking conditions are, for example, from 40 ° C to 120 ° C for 0.1 minutes to 5 minutes. The post-baking conditions are carried out at 120 ° C to 230 ° C, preferably 150 ° C to 200 ° C, more preferably 150 ° C to 180 ° C for 5 minutes to 200 minutes, preferably 10 minutes to 100 minutes. The film thickness of the coating film after post-baking is preferably 0.001 μm to 1 μm, more preferably 0.005 μm to 0.5 μm, still more preferably 0.01 μm to 0.3 μm.
將液晶配向劑塗布於基板上時所使用的液晶配向劑的固形物濃度(液晶配向劑的除溶劑以外的成分的合計重量在液晶配向劑的總重量中所占的比例)可考慮黏性、揮發性等而適宜選擇,優選為1 wt%~10 wt%的範圍,理想的是根據塗布液晶配向劑的方法而適宜選擇。 The solid content concentration of the liquid crystal alignment agent used when the liquid crystal alignment agent is applied to the substrate (the ratio of the total weight of the components other than the solvent of the liquid crystal alignment agent to the total weight of the liquid crystal alignment agent) may be considered to be viscous, It is suitably selected from the viewpoint of volatility and the like, and is preferably in the range of 1 wt% to 10 wt%, and is preferably selected in accordance with a method of applying a liquid crystal alignment agent.
其次,通過對[4]步驟中所形成的塗膜照射直線偏光或 部分偏光的放射線、或非偏光的放射線而賦予液晶配向能力。如此的處理與摩擦處理等先前的配向處理的方法對應,可避免產生塵埃或損傷等問題,能夠更簡便地進行。此處,放射線例如可使用包含100 nm~400 nm的波長光的紫外線。當所使用的放射線為直線偏光或部分偏光的情況時,照射可自垂直於基板面的方向進行,也可以自斜方向進行以賦予預傾角,而且亦可將該些方法組合而進行。在照射非偏光的放射線的情況時,照射方向必需是斜方向。 Secondly, by irradiating the coating film formed in the step [4] with linear polarization or Partially polarized radiation, or non-polarized radiation, imparts liquid crystal alignment capability. Such a treatment corresponds to a method of the previous alignment treatment such as rubbing treatment, and problems such as generation of dust or damage can be avoided, and the processing can be performed more easily. Here, as the radiation, for example, ultraviolet rays containing light having a wavelength of 100 nm to 400 nm can be used. When the radiation to be used is linearly polarized or partially polarized, the irradiation may be performed from a direction perpendicular to the substrate surface, or may be performed from an oblique direction to impart a pretilt angle, or may be performed by combining the methods. In the case of irradiating non-polarized radiation, the irradiation direction must be an oblique direction.
放射線的照射量優選為1 J/m2以上且不足10,000 J/m2,更優選為10 J/m2~3,000 J/m2。放射線的照射時間優選為數秒至數小時的範圍。優選根據所使用的聚醯亞胺的種類而選擇適宜的放射線的放射量與照射時間。 The irradiation amount of the radiation is preferably 1 J/m 2 or more and less than 10,000 J/m 2 , and more preferably 10 J/m 2 to 3,000 J/m 2 . The irradiation time of the radiation is preferably in the range of several seconds to several hours. It is preferred to select a suitable amount of radiation and an irradiation time depending on the type of the polyimide used.
而且,於本實施形態的彩色濾光片在著色圖案上具有保護膜的情況下,在上述[3]步驟後且在形成ITO電極以前,實施以下的[x]步驟至[xiii]步驟而形成保護膜。 Further, when the color filter of the present embodiment has a protective film on the colored pattern, the following steps [x] to [xiii] are performed after the step [3] and before the formation of the ITO electrode. Protective film.
在通過[3]步驟而形成著色圖案後,在形成了此著色圖案的基板上的著色圖案上形成本實施形態的感放射線性樹脂組成物的塗膜。 After the colored pattern is formed by the step [3], the coating film of the radiation sensitive resin composition of the present embodiment is formed on the colored pattern on the substrate on which the colored pattern is formed.
在利用塗布法而形成塗膜的情況時,在形成了著色圖案的基板上塗布感放射線性樹脂組成物的溶液後,優選對塗布面進行預焙,由此可形成塗膜。塗布法中所使用的組成物溶液的固形物濃度優選為5質量%~50質量%,更優選為10質量%~40質量%,特別優選為15質量%~35質 量%。感放射線性樹脂組成物溶液的塗布方法例如可採用噴霧法、輥塗法、旋轉塗布法(亦稱為旋塗法或旋轉器法)、狹縫塗布法(狹縫口模塗布法)、棒式塗布法、噴墨塗布法等適宜的方法。該些塗布方法中優選旋轉塗布法或狹縫塗布法。 When a coating film is formed by a coating method, after coating a solution of a radiation sensitive resin composition on a substrate on which a colored pattern is formed, it is preferred to pre-bake the coated surface to form a coating film. The solid content concentration of the composition solution used in the coating method is preferably 5% by mass to 50% by mass, more preferably 10% by mass to 40% by mass, and particularly preferably 15% by mass to 35% by mass. the amount%. The coating method of the radiation sensitive resin composition solution can be, for example, a spray method, a roll coating method, a spin coating method (also referred to as a spin coating method or a spinner method), a slit coating method (slit die coating method), or a rod. A suitable method such as a coating method or an inkjet coating method. Among these coating methods, a spin coating method or a slit coating method is preferred.
上述預焙的條件因各成分的種類、調配比例等而異,優選為70℃~120℃,優選為1分鐘~15分鐘左右。塗膜的預焙後的膜厚優選為0.5 μm~10 μm,更優選為1.0 μm~7.0 μm左右。 The pre-baking conditions vary depending on the type of each component, the blending ratio, and the like, and are preferably from 70 ° C to 120 ° C, preferably from about 1 minute to 15 minutes. The film thickness after prebaking of the coating film is preferably from 0.5 μm to 10 μm, and more preferably from about 1.0 μm to 7.0 μm.
其次,對所形成的塗膜的至少一部分照射放射線。此時,當僅對塗膜的一部分進行照射時,例如可利用介隔具有規定圖案的光掩模而進行照射的方法。 Next, at least a part of the formed coating film is irradiated with radiation. At this time, when only a part of the coating film is irradiated, for example, a method of irradiating with a photomask having a predetermined pattern can be used.
照射中所使用的放射線可列舉可見光線、紫外線、遠紫外線等。其中優選波長處於250 nm~550 nm的範圍的放射線,更優選包含365 nm的紫外線的放射線。 Examples of the radiation used in the irradiation include visible light rays, ultraviolet rays, far ultraviolet rays, and the like. Among them, radiation having a wavelength in the range of 250 nm to 550 nm is preferable, and radiation containing ultraviolet rays of 365 nm is more preferable.
放射線照射量(曝光量)是利用照度計(OAI model 356、Optical Associates Inc.製造)而測定所照射的放射線的波長365 nm下的強度的值,優選100 J/m2~5,000 J/m2,更優選200 J/m2~3,000 J/m2。 The radiation exposure amount (exposure amount) is a value obtained by measuring the intensity at the wavelength of 365 nm of the irradiated radiation by an illuminometer (OAI model 356, manufactured by Optical Associates Inc.), and preferably 100 J/m 2 to 5,000 J/m 2 . More preferably, it is 200 J/m 2 - 3,000 J/m 2 .
本實施形態的彩色濾光片的保護膜形成中所使用的感放射線性樹脂組成物具有如下的優點:與先前已知的保護膜形成的組成物相比而言放射線感光度更高。因此,即使在上述放射線照射量為700 J/m2以下、進一步為600 J/m2 以下時,亦可獲得所期望的膜厚、良好的形狀、優異的密接性及高硬度的保護膜。 The radiation sensitive resin composition used in the formation of the protective film of the color filter of the present embodiment has an advantage that the radiation sensitivity is higher than that of the composition formed by the previously known protective film. Therefore, even when the radiation irradiation amount is 700 J/m 2 or less and further 600 J/m 2 or less, a desired film thickness, a good shape, excellent adhesion, and a high hardness protective film can be obtained.
其次,通過對放射線照射後的感放射線性樹脂組成物的塗膜進行顯影,除去不必要的部分,形成規定的圖案。 Next, the coating film of the radiation sensitive resin composition after the radiation irradiation is developed to remove unnecessary portions, thereby forming a predetermined pattern.
顯影中所使用的顯影液例如可使用氫氧化鈉、氫氧化鉀、碳酸鈉等無機鹼,四甲基氫氧化銨、四乙基氫氧化銨等季銨鹽等鹼性化合物的水溶液。上述鹼性化合物的水溶液中亦可添加適當量的甲醇、乙醇等水溶性有機溶劑而使用。另外,亦可僅僅添加適當量的界面活性劑而使用,或者將適當量的界面活性劑與上述水溶性有機溶劑一同添加而使用。 For the developer to be used for development, for example, an inorganic base such as sodium hydroxide, potassium hydroxide or sodium carbonate, or an aqueous solution of a basic compound such as a quaternary ammonium salt such as tetramethylammonium hydroxide or tetraethylammonium hydroxide can be used. An appropriate amount of a water-soluble organic solvent such as methanol or ethanol may be added to the aqueous solution of the basic compound. Further, it may be used by merely adding an appropriate amount of a surfactant, or by adding an appropriate amount of a surfactant together with the above-described water-soluble organic solvent.
顯影方法可為覆液法、浸漬法、噴淋法等的任意種,顯影時間優選在常溫下為10秒~180秒左右。繼顯影處理之後,例如進行30秒~90秒的流水清洗,然後用壓縮空氣或壓縮氮氣進行風乾,由此而獲得所期望的圖案。 The development method may be any of a liquid coating method, a dipping method, a shower method, and the like, and the development time is preferably about 10 seconds to 180 seconds at normal temperature. After the development treatment, for example, a running water rinse is performed for 30 seconds to 90 seconds, and then air-dried with compressed air or compressed nitrogen gas, thereby obtaining a desired pattern.
其次,通過利用熱板、烘箱等適當的加熱裝置對所得的圖案狀塗膜進行硬化(亦稱為後烘),製成硬化膜而獲得保護膜。硬化溫度優選為200℃以下。而且,即使是180℃以下亦可獲得具有充分的特性的保護膜。具體而言優選為100℃~200℃,當欲以高的水準而兼顧低溫硬化與可靠性能的情況時,更優選為150℃~180℃。作為硬化時間,例如在熱板上優選為5分鐘~30分鐘,在烘箱中優選為30 分鐘~180分鐘。感放射線性樹脂組成物如上所述那樣含有[D]化合物,因此可實現如此低的低溫硬化。而且,可實現保存穩定性,且具有充分的分辨率及放射線感光度。 Next, the obtained pattern-like coating film is cured (also referred to as post-baking) by a suitable heating means such as a hot plate or an oven to obtain a cured film to obtain a protective film. The hardening temperature is preferably 200 ° C or lower. Further, a protective film having sufficient characteristics can be obtained even at 180 ° C or lower. Specifically, it is preferably 100° C. to 200° C., and when it is desired to achieve both low-temperature curing and reliability at a high level, it is more preferably 150° C. to 180° C. As the hardening time, for example, it is preferably 5 minutes to 30 minutes on a hot plate, and preferably 30 in an oven. Minutes ~ 180 minutes. The radiation sensitive resin composition contains the [D] compound as described above, and thus such low low temperature hardening can be achieved. Moreover, storage stability can be achieved with sufficient resolution and radiation sensitivity.
因此,感放射線性樹脂組成物在形成保護膜的情況中,作為保護膜(所述保護膜與使用低溫硬化較為理想的染料的著色圖案組合使用)的形成材料而適宜地使用。 Therefore, in the case where the radiation-sensitive resin composition is formed, it is suitably used as a material for forming a protective film (the protective film is used in combination with a colored pattern of a dye which is preferably used for low-temperature curing).
依照以上的製造方法,可製造著色圖案、保護膜及配向膜,且可製造本實施形態的彩色濾光片。如上所述,本實施形態的彩色濾光片的著色圖案是將著色組成物塗布於適當的基板上並進行圖案化後,進行硬化而形成。保護膜也同樣地塗布感放射線性樹脂組成物並進行圖案化後,進行硬化而形成。而且,著色組成物及感放射線性樹脂組成物均可如上所述那樣利用200℃以下的低溫硬化而形成著色圖案與保護膜。 According to the above manufacturing method, a colored pattern, a protective film, and an alignment film can be produced, and the color filter of this embodiment can be manufactured. As described above, the coloring pattern of the color filter of the present embodiment is formed by applying a colored composition onto a suitable substrate, patterning, and then curing. The protective film is similarly coated with a radiation sensitive resin composition, patterned, and then cured. Further, the colored composition and the radiation-sensitive resin composition can be formed into a colored pattern and a protective film by low-temperature curing at 200 ° C or lower as described above.
因此,於本實施形態的彩色濾光片中,可利用200℃以下的低溫硬化而形成著色圖案,即使在具有保護膜的情況下,亦可利用200℃以下的低溫硬化而形成保護膜,可進行低溫硬化的製造。 Therefore, in the color filter of the present embodiment, the colored pattern can be formed by low-temperature curing at 200 ° C or lower, and even when the protective film is provided, the protective film can be formed by low-temperature curing at 200 ° C or lower. Manufacturing of low temperature hardening.
而且,於本實施形態的彩色濾光片中,保護膜可利用200℃以下的低溫硬化而形成,因此著色圖案在形成後並不暴露於用以形成保護膜的高溫加熱的狀態下。因此,即使使用雖然顏色特性優異但於耐熱性上存在問題的染料作為著色劑,亦可減低步驟劣化。 Further, in the color filter of the present embodiment, since the protective film can be formed by low-temperature curing at 200 ° C or lower, the colored pattern is not exposed to the high-temperature heating for forming the protective film after the formation. Therefore, even if a dye having excellent color properties but having problems in heat resistance is used as a colorant, step deterioration can be reduced.
另外,如上所述,著色組成物與感放射線性樹脂組成 物均可設為使用同類的材料的感放射線性樹脂組成物。因此,於製造本實施形態的彩色濾光片時的形成著色圖案時,可考慮其後的保護膜形成而調整硬化溫度。亦即,利用與最適於在基板上單獨形成著色圖案的硬化溫度相比而言更低的硬化溫度而形成著色圖案。其後,通過著色圖案上所形成的保護膜的硬化加熱,亦可對著色圖案進行加熱。 In addition, as described above, the coloring composition is composed of a radiation-sensitive resin The material can be set to a radiation-sensitive resin composition using a similar material. Therefore, when the colored pattern is formed in the production of the color filter of the present embodiment, the curing temperature can be adjusted in consideration of the formation of the subsequent protective film. That is, the colored pattern is formed using a lower curing temperature than the curing temperature most suitable for separately forming a colored pattern on the substrate. Thereafter, the colored pattern may be heated by hardening and heating of the protective film formed on the colored pattern.
因此,在著色圖案與保護膜的最適宜的硬化溫度分別為例如200℃以下、具體而言為180℃的情況時,可預先在150℃的硬化溫度下形成著色圖案。其次,在該著色圖案上形成感放射線性樹脂組成物的塗膜,在最適宜的180℃下進行硬化,由此而形成保護膜。其結果,形成在其下層的著色圖案也受到加熱,變得可獲得包含所期望的狀態的著色圖案與保護膜的本實施形態的彩色濾光片。 Therefore, when the optimum curing temperature of the colored pattern and the protective film is, for example, 200 ° C or lower, specifically 180 ° C, the colored pattern can be formed in advance at a curing temperature of 150 ° C. Next, a coating film of a radiation-sensitive resin composition is formed on the colored pattern, and is cured at an optimum temperature of 180 ° C to form a protective film. As a result, the colored pattern formed in the lower layer is also heated, and the color filter of the present embodiment including the colored pattern and the protective film in a desired state can be obtained.
而且,於本實施形態的彩色濾光片中,在具有保護膜的情況下,保護膜可實現電氣特性或可靠性等優異的ITO電極。而且,保護膜對著色圖案進行覆蓋,可保護作為著色圖案的著色劑的染料免受於配向膜的光配向處理中所照射的紫外線等。 Further, in the color filter of the present embodiment, when the protective film is provided, the protective film can realize an ITO electrode excellent in electrical characteristics, reliability, and the like. Further, the protective film covers the colored pattern, and the dye which is a coloring agent of the colored pattern can be protected from ultraviolet rays or the like which are irradiated during the photoalignment treatment of the alignment film.
以下,基於實例對本發明的實施形態加以詳述,但並不以該實例而對本發明進行限定性解釋。 Hereinafter, the embodiments of the present invention will be described in detail based on examples, but the present invention is not limited by the examples.
在具有冷凝管及攪拌機的燒瓶中裝入2,2'-偶氮雙(2,4-二甲基戊腈)5質量份及二乙二醇甲乙醚220質量份。其次,裝入作為(I-1)化合物的甲基丙烯酸18質量份、作為(I-2)化合物的甲基丙烯酸-2-甲基縮水甘油酯14質量份及甲基丙烯酸縮水甘油酯20質量份、作為(I-4)化合物的苯乙烯10質量份、甲基丙烯酸三環[5.2.1.02,6]癸烷-8-基酯23質量份及甲基丙烯酸甲酯15質量份,進行氮氣置換後,一面緩緩地攪拌一面使溶液的溫度上升至70℃,保持該溫度5小時而進行聚合,由此而獲得含有作為共聚物的鹼溶性樹脂(IA)的溶液。所得的聚合物溶液的固形物濃度為31.5%,作為共聚物的鹼溶性樹脂(IA)的Mw為10,100。 In a flask equipped with a condenser and a stirrer, 5 parts by mass of 2,2'-azobis(2,4-dimethylvaleronitrile) and 220 parts by mass of diethylene glycol methyl ethyl ether were placed. Next, 18 parts by mass of methacrylic acid as a compound (I-1), 14 parts by mass of 2-methylglycidyl methacrylate as a compound of (I-2), and 20 mg of glycidyl methacrylate. And 10 parts by mass of styrene as the compound (I-4), 23 parts by mass of tricyclo [5.2.1.0 2,6 ]decane-8-yl methacrylate, and 15 parts by mass of methyl methacrylate. After the nitrogen gas was replaced, the temperature of the solution was gradually raised to 70 ° C while stirring, and the temperature was maintained for 5 hours to carry out polymerization, whereby a solution containing an alkali-soluble resin (IA) as a copolymer was obtained. The solid solution concentration of the obtained polymer solution was 31.5%, and the Mw of the alkali-soluble resin (IA) as a copolymer was 10,100.
在具有冷凝管及攪拌機的燒瓶中裝入AIBN4質量份及二乙二醇甲乙醚300質量份,其次裝入作為(I-1)化合物的甲基丙烯酸23質量份、作為(I-4)化合物的苯乙烯10質量份、甲基丙烯酸苄基酯32質量份及甲基丙烯酸甲酯35質量份,進一步裝入α-甲基苯乙烯二聚物2.7質量份,一面緩緩地攪拌一面使溶液的溫度上升至80℃,保持該溫度4小時後使其上升至100℃,保持該溫度1小時而進行聚合,由此而獲得含有共聚物的溶液。所得的聚合物溶液的固形物濃度為24.9%,Mw為12,500。其次,在所得的包含共聚物的溶液中加入四丁基溴化銨1.1質量份、 作為聚合抑制劑的4-甲氧基苯酚0.05質量份,在空氣環境下、90℃下攪拌30分鐘後,放入作為(I-2)化合物的甲基丙烯酸縮水甘油酯16質量份而保持90℃使其反應10小時,由此而獲得作為共聚物的鹼溶性樹脂(IB)。所得的聚合物溶液的固形物濃度為29.0%,Mw為14,200。 4 parts by mass of AIBN and 300 parts by mass of diethylene glycol methyl ethyl ether were placed in a flask equipped with a condenser and a stirrer, and 23 parts by mass of methacrylic acid as a compound (I-1) was added thereto as a compound (I-4). 10 parts by mass of styrene, 32 parts by mass of benzyl methacrylate, and 35 parts by mass of methyl methacrylate, further charged with 2.7 parts by mass of α-methylstyrene dimer, and slowly stirred while stirring The temperature was raised to 80 ° C, and after maintaining the temperature for 4 hours, the temperature was raised to 100 ° C, and the temperature was maintained for 1 hour to carry out polymerization, whereby a solution containing a copolymer was obtained. The resulting polymer solution had a solids concentration of 24.9% and a Mw of 12,500. Next, 1.1 parts by mass of tetrabutylammonium bromide is added to the obtained solution containing the copolymer, 0.05 parts by mass of 4-methoxyphenol as a polymerization inhibitor, and after stirring at 90 ° C for 30 minutes in an air atmosphere, 16 parts by mass of glycidyl methacrylate as a compound (I-2) was placed and kept at 90%. The reaction was carried out for 10 hours at ° C, whereby an alkali-soluble resin (IB) as a copolymer was obtained. The obtained polymer solution had a solid concentration of 29.0% and a Mw of 14,200.
相對於實例1中所得的作為共聚物的鹼溶性樹脂(IA)90質量份而混合作為[II]聚合性化合物的環氧乙烷改質二季戊四醇六丙烯酸酯(II-1)與多官能丙烯酸酯化合物的混合物(KAYARAD(注冊商標)DPHA-40H、日本化藥公司)(II-2)的混合物(混合比率((II-1)/(II-2))=4)100質量份、作為[III]聚合起始劑的2-甲基-1-(4-甲基噻吩基)-2-嗎啉代丙烷-1-酮(Irgacure 907、汽巴精化有限公司)(III-1)25質量份、作為[IV]著色劑的包含紅色染料的紅色著色劑(IV-1)100質量份、作為[V]化合物的季戊四醇四(3-巰基丙酸)酯(V-1)與3-胺基苯磺酸乙酯(V-2)的混合物(混合比率((V-1)/(V-2)=5))6質量份、作為其他鹼溶性樹脂的實例2中所得的鹼溶性樹脂(IB)10質量份。其次,使用環己酮作為溶劑,以著色組成物的固形物濃度成為30質量%的方式添加溶劑後,利用孔徑為0.5 μm的微孔過濾器進行過濾,由此而調製紅色著色組成物。 Ethylene oxide-modified dipentaerythritol hexaacrylate (II-1) and polyfunctional acrylic acid as a [II] polymerizable compound were mixed with 90 parts by mass of the alkali-soluble resin (IA) as a copolymer obtained in Example 1. a mixture of a mixture of ester compounds (KAYARAD (registered trademark) DPHA-40H, Nippon Kayaku Co., Ltd.) (II-2) (mixing ratio ((II-1) / (II-2)) = 4) 100 parts by mass, as [III] 2-methyl-1-(4-methylthienyl)-2-morpholinopropan-1-one (Irgacure 907, Ciba Specialty Chemicals Co., Ltd.) (III-1) as a polymerization initiator 25 parts by mass, 100 parts by mass of a red coloring agent (IV-1) containing a red dye as a [IV] coloring agent, pentaerythritol tetrakis(3-mercaptopropionate) (V-1) as a compound of [V] and 3 parts by weight a mixture of ethylaminobenzenesulfonate (V-2) (mixing ratio ((V-1) / (V-2) = 5)) 6 parts by mass, the base obtained in Example 2 as another alkali-soluble resin The soluble resin (IB) was 10 parts by mass. Next, cyclohexanone was used as a solvent, and a solvent was added so that the solid content concentration of the coloring composition became 30% by mass, and then filtered using a micropore filter having a pore diameter of 0.5 μm to prepare a red colored composition.
除了使用包含綠色染料的綠色著色劑(IV-2)作為[IV] 著色劑以外,與上述同樣地進行而調製綠色著色組成物。而且,除了使用包含藍色染料的藍色著色劑(IV-3)作為[IV]著色劑以外,與上述同樣地進行而調製藍色著色組成物。 In addition to using green colorant (IV-2) containing green dye as [IV] Other than the colorant, the green coloring composition was prepared in the same manner as described above. Further, a blue coloring composition was prepared in the same manner as above except that a blue coloring agent (IV-3) containing a blue dye was used as the [IV] coloring agent.
在表面上形成有防止鈉離子溶出的SiO2膜的鈉玻璃基板上,使用旋塗機而塗布實例3中所得的紅色著色組成物。其次,在90℃的熱板上進行2分鐘的預焙,形成預焙後的膜厚為2.5 μm的塗膜。將該些基板冷卻至室溫後,使用高壓水銀燈,介隔光掩模以1,000 J/m2的曝光量對塗膜曝光包含365 nm、405 nm及436 nm的各波長的放射線。其後,以顯影壓力1 kgf/cm2(管嘴直徑為1 mm)而對該些基板噴出顯影液(23℃的0.04質量%氫氧化鉀水溶液),由此進行噴淋顯影,而在基板上形成200 μm×200 μm的著色圖案。進一步在180℃下進行30分鐘的後烘而形成紅色的著色圖案。 On the soda glass substrate on which the SiO 2 film for preventing elution of sodium ions was formed on the surface, the red colored composition obtained in Example 3 was applied using a spin coater. Next, prebaking was performed on a hot plate at 90 ° C for 2 minutes to form a coating film having a film thickness of 2.5 μm after prebaking. After the substrates were cooled to room temperature, radiation of respective wavelengths of 365 nm, 405 nm, and 436 nm was exposed to the coating film at a exposure amount of 1,000 J/m 2 using a high pressure mercury lamp through a photomask. Thereafter, a developing solution (a 0.04 mass% potassium hydroxide aqueous solution at 23 ° C) was sprayed onto the substrates at a developing pressure of 1 kgf/cm 2 (nozzle diameter of 1 mm) to thereby perform shower development on the substrate. A colored pattern of 200 μm × 200 μm was formed thereon. Further, post-baking was performed at 180 ° C for 30 minutes to form a red colored pattern.
使用實例3中所得的綠色著色組成物作為著色組成物,除此以外與上述同樣地進行而形成綠色的著色圖案。而且,使用實例3中所得的藍色著色組成物作為著色組成物,除此以外與上述同樣地進行而形成藍色的著色圖案。 A green coloring pattern was formed in the same manner as described above except that the green coloring composition obtained in Example 3 was used as the coloring composition. Further, a blue coloring pattern was formed in the same manner as described above except that the blue coloring composition obtained in Example 3 was used as the coloring composition.
對所製造的著色圖案進行下述的評價。 The following coloring patterns were evaluated.
在上述各色的著色圖案的形成中,算出下述式的值:顯影前後的膜厚比=(顯影後的膜厚/顯影前的膜厚)×100。 In the formation of the color pattern of each of the above colors, the value of the following formula was calculated: the film thickness ratio before and after development = (film thickness after development / film thickness before development) × 100.
上述各色的著色圖案均是顯影前後的膜厚比為95%以上,可知具有良好的耐顯影性。 The coloring pattern of each of the above colors was 95% or more in thickness before and after development, and it was found that the coloring resistance was excellent.
對上述各色的著色圖案進一步在180℃下追加加熱30分鐘。而且求出追加加熱前後的顏色變化△Eab*。上述各色的著色圖案均是△Eab*不足3,可知具有良好的耐熱性。 The coloring pattern of each of the above colors was further heated at 180 ° C for additional 30 minutes. Further, the color change ΔEab * before and after the additional heating is obtained. The coloring patterns of the respective colors described above were all ΔEab * less than 3, and it was found to have good heat resistance.
關於上述著色圖案,與基板一同浸漬於60℃的N-甲基吡咯烷酮中30分鐘。其後,觀察基板上的各色的著色圖案,結果確認均在浸漬後保持著色圖案,且浸漬後的N-甲基吡咯烷酮完全不著色。可知上述任意著色圖案均耐溶劑性良好。 The colored pattern was immersed in N-methylpyrrolidone at 60 ° C for 30 minutes together with the substrate. Thereafter, the coloring patterns of the respective colors on the substrate were observed, and as a result, it was confirmed that the coloring pattern was maintained after the immersion, and the immersed N-methylpyrrolidone was not colored at all. It is understood that any of the above colored patterns has good solvent resistance.
在具有冷凝管及攪拌機的燒瓶中裝入2,2'-偶氮雙(2,4-二甲基戊腈)7質量份及二乙二醇甲乙醚200質量份。其次裝入甲基丙烯酸16質量份、甲基丙烯酸三環[5.2.1.02,6]癸 烷-8-基酯16質量份、甲基丙烯酸甲酯38質量份、苯乙烯10質量份、甲基丙烯酸縮水甘油酯20質量份,進行氮氣置換後,一面緩緩地攪拌一面使溶液的溫度上升至70℃,將該溫度保持4小時而進行聚合,由此而獲得含有共聚物(A-1)的溶液(固形物濃度=34.4質量%、Mw=8,000、Mw/Mn=2.3)。另外,固形物濃度是表示共聚物的質量在共聚物溶液的總質量中所占的比例。 In a flask equipped with a condenser and a stirrer, 7 parts by mass of 2,2'-azobis(2,4-dimethylvaleronitrile) and 200 parts by mass of diethylene glycol methyl ethyl ether were charged. Next, 16 parts by mass of methacrylic acid, 16 parts by mass of tricyclo [5.2.1.0 2,6 ]decane-8-yl methacrylate, 38 parts by mass of methyl methacrylate, and 10 parts by mass of styrene, A were charged. 20 parts by mass of glycidyl acrylate, after nitrogen substitution, the temperature of the solution was gradually increased to 70 ° C while stirring slowly, and the temperature was maintained for 4 hours to carry out polymerization, thereby obtaining a copolymer (A-1). (Solid concentration = 34.4% by mass, Mw = 8,000, Mw / Mn = 2.3). Further, the solid concentration is a ratio indicating the mass of the copolymer in the total mass of the copolymer solution.
相對於作為[A]化合物的實例6中所得的共聚物(A-1)100質量份,混合作為[B]聚合性化合物的二季戊四醇六丙烯酸酯(B-1)100質量份、作為[C]聚合起始劑的乙酮-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-哢唑-3-基]-1-(O-乙醯肟)(Irgacure OXE02、汽巴精化有限公司)(C-1)5質量份、及作為[D]化合物的4,4'-二胺基二苯基碸(D-1),進一步混合作為[J-1]接著助劑的γ-縮水甘油氧基丙基三甲氧基矽烷5質量份、[J-2]界面活性劑(FTX-218、Neos公司)0.5質量份、作為[J-3]保存穩定劑的4-甲氧基苯酚0.5質量份,以固形物濃度成為30質量%的方式分別加入丙二醇單甲醚乙酸酯後,利用孔徑為0.5 μm的微孔過濾器進行過濾,由此而調製感放射線性樹脂組成物。 100 parts by mass of dipentaerythritol hexaacrylate (B-1) as a [B] polymerizable compound was mixed with 100 parts by mass of the copolymer (A-1) obtained in Example 6 as the compound [A] as [C] Ethylketone-1-[9-ethyl-6-(2-methylbenzhydryl)-9H-indazol-3-yl]-1-(O-acetamidine) of the polymerization initiator Irgacure OXE02, Ciba Specialty Chemicals Co., Ltd.) (C-1) 5 parts by mass, and 4,4'-diaminodiphenyl hydrazine (D-1) as a compound of [D], further mixed as [J- 1] 5 parts by mass of γ-glycidoxypropyltrimethoxydecane followed by auxiliary agent, 0.5 parts by mass of [J-2] surfactant (FTX-218, Neos), and stable as [J-3] 0.5 parts by mass of the 4-methoxyphenol of the agent, and propylene glycol monomethyl ether acetate was added thereto so that the solid content concentration was 30% by mass, and then filtered by a micropore filter having a pore diameter of 0.5 μm, thereby preparing A radiation sensitive resin composition.
利用旋轉器將實例7中所調製的感放射線性樹脂組成 物溶液塗布於無鹼玻璃基板上之後,在100℃的熱板上進行2分鐘的預焙而形成膜厚為4.0 μm的塗膜。其次,使用高壓水銀燈使曝光量為700 J/m2而對所得的塗膜進行放射線照射。其次,在烘箱中,在180℃的硬化溫度及30分鐘的硬化時間的條件下進行後烘而形成保護膜。 The radiation-sensitive resin composition solution prepared in Example 7 was applied onto an alkali-free glass substrate by a spinner, and then prebaked on a hot plate at 100 ° C for 2 minutes to form a coating film having a film thickness of 4.0 μm. Next, the obtained coating film was irradiated with radiation by using a high pressure mercury lamp so that the exposure amount was 700 J/m 2 . Next, post-baking was carried out in an oven at a curing temperature of 180 ° C and a hardening time of 30 minutes to form a protective film.
由剛調製之後的實例7的感放射線性樹脂組成物溶液,通過實例8的形成方法而形成保護膜,測定膜厚(在下述式中稱為“剛調製之後的膜厚”)。而且,利用實例7的形成方法而進行調製後,在25℃下保存感放射線性樹脂組成物溶液5天,在5天後同樣地測定所形成的保護膜的膜厚(在下述式中稱為“5天後的膜厚”)。根據下述式算出膜厚增加率(%)。 A protective film was formed by the formation method of Example 8 from the radiation-sensitive resin composition solution of Example 7 immediately after preparation, and the film thickness (referred to as "film thickness immediately after preparation" in the following formula) was measured. Further, after the preparation was carried out by the formation method of Example 7, the radiation sensitive resin composition solution was stored at 25 ° C for 5 days, and the film thickness of the formed protective film was measured in the same manner after 5 days (referred to as the following formula). "Film thickness after 5 days"). The film thickness increase rate (%) was calculated from the following formula.
膜厚增加率(%)=(5天後的膜厚-剛調製之後的膜厚)/(剛調製之後的膜厚)×100 Film thickness increase rate (%) = (film thickness after 5 days - film thickness immediately after preparation) / (film thickness immediately after preparation) × 100
膜厚增加率為3%以下,從而判斷保存穩定性良好。 The film thickness increase rate was 3% or less, and it was judged that the storage stability was good.
關於利用實例8的形成方法所得的保護膜,進一步用UV照射裝置(UVX-02516S1JS01、Ushio Inc.)而以130 mW的照度進行800,000 J/m2的照射,檢查膜減少量。膜減少 量為2%以下,從而判斷耐光性良好 The protective film obtained by the method of the formation of Example 8 was further irradiated with 800,000 J/m 2 at an illuminance of 130 mW using a UV irradiation apparatus (UVX-02516S1JS01, Ushio Inc.) to examine the amount of film reduction. The film reduction amount is 2% or less, so that the light resistance is judged to be good
關於利用實例8的形成方法所得的保護膜,進一步在烘箱中、230℃下加熱20分鐘,用觸針式膜厚測定機(Alpha Step IQ、美商科磊(KLA-TENCOR)公司)測定其加熱前後的膜厚。而且算出殘膜率(處理後的膜厚/處理前的膜厚×100),將該殘膜率作為耐熱性。殘膜率為99%,從而判斷耐熱性良好。 The protective film obtained by the formation method of Example 8 was further heated in an oven at 230 ° C for 20 minutes, and the heating was measured by a stylus type film thickness measuring machine (Alpha Step IQ, KLA-TENCOR Co., Ltd.). Film thickness before and after. Further, the residual film ratio (film thickness after treatment/film thickness before treatment × 100) was calculated, and the residual film ratio was taken as heat resistance. The residual film ratio was 99%, and it was judged that the heat resistance was good.
關於利用實例8的形成方法所得的保護膜,在加溫至60℃的配向膜剝離液CHEMICLEAN(注冊商標)TS-204(三洋化成工業公司)中浸漬15分鐘,加以水洗後,進一步在烘箱中、120℃下乾燥15分鐘。用觸針式膜厚測定機(Alpha Step IQ、美商科磊公司)測定該處理前後的膜厚,算出殘膜率(處理後的膜厚/處理前的膜厚×100),將該殘膜率作為耐化學品性。殘膜率為99%,從而判斷耐化學品性良好。 The protective film obtained by the formation method of Example 8 was immersed in an aligning film stripping solution CHEMICLEAN (registered trademark) TS-204 (Sanyo Chemical Industry Co., Ltd.) heated to 60 ° C for 15 minutes, washed with water, and further in an oven. Dry at 120 ° C for 15 minutes. The film thickness before and after the treatment was measured by a stylus type film thickness measuring machine (Alpha Step IQ, Meike), and the residual film ratio (film thickness after treatment/film thickness before treatment × 100) was calculated, and the residual film was obtained. Rate as chemical resistance. The residual film ratio was 99%, and it was judged that the chemical resistance was good.
於反應容器中裝入作為溶劑的N-甲基吡咯烷酮(以下簡稱為NMP),並且裝入2,2-雙[4-(4-胺基苯氧基)苯基]丙烷100質量份與1,2,3,4,-環丁烷四甲酸二酐47質量份,於NMP中、室溫下進行10小時的反應,調製作為聚醯亞胺前驅物的聚醯胺酸溶液。進一步用NMP對該溶液進行 稀釋,調整固形物濃度而獲得液晶配向劑。 N-methylpyrrolidone (hereinafter abbreviated as NMP) as a solvent was placed in a reaction vessel, and 100 parts by mass of 2,2-bis[4-(4-aminophenoxy)phenyl]propane was charged and 1 47 parts by mass of 2,3,4,-cyclobutanetetracarboxylic dianhydride was reacted in NMP at room temperature for 10 hours to prepare a polyaminic acid solution as a polyimide precursor. Further using NMP to carry out the solution Dilute and adjust the solid concentration to obtain a liquid crystal alignment agent.
使用實例3中所說明的各色著色組成物(紅色著色組成物、綠色著色組成物及藍色著色組成物)而製造彩色濾光片。首先,利用狹縫口模塗布機在形成有黑色矩陣圖案的玻璃基板上塗布紅色著色組成物,在熱板上、90℃下進行2分鐘的預焙而形成塗膜。其後,介隔規定的圖案掩模,使用曝光機Canon PLA501F(佳能公司)而照射以i線換算計而言為1,000 J/m2的曝光量的ghi線(波長為436 nm、405 nm、365 nm的強度比=2.7:2.5:4.8),使用0.05%氫氧化鉀水溶液而進行顯影,於超純水中進行60秒的沖洗,然後進一步在烘箱中、180℃下進行30分鐘的加熱處理,形成膜厚為2.0 μm的紅色的著色圖案(圖案寬度為100 μm)。 A color filter was produced using the coloring compositions of the respective colors (the red coloring composition, the green coloring composition, and the blue coloring composition) described in Example 3. First, a red colored composition was applied onto a glass substrate on which a black matrix pattern was formed by a slit die coater, and pre-baked on a hot plate at 90 ° C for 2 minutes to form a coating film. Thereafter, a ghi line (wavelength of 436 nm, 405 nm, and an exposure amount of 1,000 J/m 2 in terms of i-line conversion was irradiated with an exposure machine Canon PLA501F (Canon Inc.) in accordance with a predetermined pattern mask. Intensity ratio at 365 nm = 2.7:2.5:4.8), development was carried out using a 0.05% aqueous potassium hydroxide solution, rinsing in ultrapure water for 60 seconds, and further heat treatment in an oven at 180 ° C for 30 minutes. A red colored pattern (pattern width of 100 μm) having a film thickness of 2.0 μm was formed.
其次,同樣地進行操作,使用綠色著色組成物而形成綠色的著色圖案。進一步使用藍色著色組成物而形成藍色的著色圖案,形成紅、綠、及藍的3色彩色濾光片。上述所形成的在後烘溫度為180℃、30分鐘的條件下所形成的紅色、綠色、藍色的3色著色圖案並不產生硬化不充分所造成的圖案缺損、自基板上剝落等問題,可形成3色的著色圖案。 Next, the operation was carried out in the same manner, and a green coloring pattern was formed using a green coloring composition. Further, a blue coloring composition was used to form a blue coloring pattern, and three color filters of red, green, and blue were formed. The red, green, and blue three-color coloring patterns formed under the conditions of the post-baking temperature of 180 ° C and 30 minutes formed as described above do not cause problems such as pattern defects caused by insufficient curing, peeling off from the substrate, and the like. A three-color coloring pattern can be formed.
其次,在所得的3色著色圖案上,通過狹縫口模塗布機而塗布實例7中所調製的感放射線性樹脂組成物。其 次,於熱板上、90℃下進行5分鐘的預焙而形成塗膜。其次,使用高壓水銀燈將曝光量設為700 J/m2而對所得的塗膜進行放射線照射,對放射線照射後的塗膜進行顯影,由此而除去不需要的部分,形成規定形狀的塗膜。進一步於烘箱中、180℃下進行60分鐘的加熱處理,形成自3色著色圖案的上表面起膜厚為2.0 μm的保護膜。如上所述地進行而製造於著色圖案上形成有保護膜的基板。 Next, on the obtained three-color coloring pattern, the radiation-sensitive resin composition prepared in Example 7 was applied by a slit die coater. Next, prebaking was performed on a hot plate at 90 ° C for 5 minutes to form a coating film. Then, the obtained coating film is irradiated with radiation by using a high-pressure mercury lamp to have an exposure amount of 700 J/m 2 , and the coating film after the radiation irradiation is developed to remove unnecessary portions, thereby forming a coating film having a predetermined shape. . Further, heat treatment was carried out in an oven at 180 ° C for 60 minutes to form a protective film having a film thickness of 2.0 μm from the upper surface of the three-color colored pattern. The substrate on which the protective film was formed on the colored pattern was produced as described above.
關於所得的在著色圖案上形成有保護膜的基板,使用接觸式膜厚測定裝置α-Step(科磊日本公司)而測定保護膜表面的凹凸(平坦性)(測定長度為2,000 μm、測定範圍為2,000 μm見方、測定點數n=5)。亦即,使測定方向為紅、綠、藍方向的著色圖案短軸方向及紅-紅、綠-綠、藍-藍的同一色的著色圖案長軸方向這2個方向,對各方向以n=5而進行測定(合計的n數為10)。求出每個測定的最高部與最低部的高低差(nm)的10次的平均值。此時的平均值為220 nm。即使在形成保護膜後,著色圖案亦不收縮、膨脹,保護膜表面無凹凸,顯示出良好的平坦性。 The substrate having the protective film formed on the colored pattern was measured for the unevenness (flatness) of the surface of the protective film using a contact-type film thickness measuring device α-Step (Keide Japan Co., Ltd.) (measurement length was 2,000 μm, measurement range) It is 2,000 μm square, and the number of measurement points is n=5). In other words, the measurement direction is the short axis direction of the color pattern in the red, green, and blue directions, and the long axis direction of the color pattern of the same color of red-red, green-green, and blue-blue, and the direction is n for each direction. The measurement was carried out at =5 (the total number of n was 10). The average of 10 times of the height difference (nm) of the highest part and the lowest part of each measurement was calculated. The average value at this time is 220 nm. Even after the formation of the protective film, the colored pattern does not shrink or swell, and the surface of the protective film has no unevenness, and exhibits good flatness.
其次,使用在著色圖案上形成有保護膜的基板,使用濺射法在保護膜上形成ITO膜,從而形成ITO電極。 Next, an ITO film was formed on the protective film by a sputtering method using a substrate on which a protective film was formed on the colored pattern to form an ITO electrode.
其次,使用實例10中所調製的液晶配向劑,用旋轉器將其塗布於在著色圖案上形成有保護膜的基板上的ITO電極上。其次,在80℃的熱板上進行1分鐘的預焙後,在對內部進行了氮氣置換的烘箱中、180℃下進行1小時的加熱而形成膜厚為80 nm的塗膜。其次,自相對於垂直於基 板表面的方向而言傾斜40度的方向對該塗膜表面照射偏光紫外線,製造具有光配向膜的彩色濾光片。 Next, using the liquid crystal alignment agent prepared in Example 10, it was applied by a spinner onto an ITO electrode on a substrate on which a protective film was formed on a colored pattern. Next, after prebaking for 1 minute on a hot plate at 80 ° C, it was heated in an oven which was internally purged with nitrogen at 180 ° C for 1 hour to form a coating film having a film thickness of 80 nm. Secondly, since it is perpendicular to the base The surface of the coating film was irradiated with polarized ultraviolet rays in a direction inclined by 40 degrees in the direction of the surface of the sheet to produce a color filter having a photoalignment film.
以如上方式而製造本實例的彩色濾光片。所製造的本實例的彩色濾光片具有優異的顏色特性。 The color filter of the present example was fabricated in the above manner. The color filter of the present example produced has excellent color characteristics.
使用實例11中所得的具有進行了光配向處理的配向膜的彩色濾光片,製造彩色液晶顯示元件。所製造的液晶顯示元件具有與上述圖3中所示的液晶顯示元件相同的結構。本實例的液晶顯示元件中,實現無缺陷的液晶配向,且顯示優異的顯示特性與可靠性能。 A color liquid crystal display element was produced using the color filter having the alignment film subjected to the photoalignment treatment obtained in Example 11. The liquid crystal display element manufactured has the same structure as the liquid crystal display element shown in FIG. 3 described above. In the liquid crystal display element of the present example, defect-free liquid crystal alignment is realized, and excellent display characteristics and reliability performance are exhibited.
本發明的彩色濾光片可利用低溫硬化而製造,具有高的可靠性且顏色特性優異。因此,本發明的彩色濾光片可作為使用樹脂基板的可撓曲液晶顯示器用彩色濾光片、或要求高畫質的大型液晶電視用彩色濾光片而適宜地使用。 The color filter of the present invention can be produced by low-temperature curing, and has high reliability and excellent color characteristics. Therefore, the color filter of the present invention can be suitably used as a color filter for a flexible liquid crystal display using a resin substrate or a color filter for a large liquid crystal television requiring high image quality.
1‧‧‧液晶顯示元件 1‧‧‧Liquid display components
2、5‧‧‧基板 2, 5‧‧‧ substrate
3‧‧‧像素電極 3‧‧‧pixel electrode
4‧‧‧ITO電極 4‧‧‧ITO electrodes
6‧‧‧著色圖案 6‧‧‧Coloring pattern
7‧‧‧黑色矩陣 7‧‧‧Black matrix
8‧‧‧保護膜 8‧‧‧Protective film
10、20‧‧‧彩色濾光片 10, 20‧‧‧ color filters
12‧‧‧配向膜 12‧‧‧Alignment film
13‧‧‧液晶 13‧‧‧LCD
14‧‧‧偏光板 14‧‧‧Polar plate
16‧‧‧密封材料 16‧‧‧ Sealing material
17‧‧‧背光源光 17‧‧‧Backlight light
圖1是本實施形態的彩色濾光片的模式剖面圖。 Fig. 1 is a schematic cross-sectional view showing a color filter of the embodiment.
圖2是本實施形態的彩色濾光片其他例的模式剖面圖。 Fig. 2 is a schematic cross-sectional view showing another example of the color filter of the embodiment.
圖3是包含本實施形態的彩色濾光片的液晶顯示元件的模式剖面圖。 Fig. 3 is a schematic cross-sectional view showing a liquid crystal display element including the color filter of the embodiment.
1‧‧‧液晶顯示元件 1‧‧‧Liquid display components
2、5‧‧‧基板 2, 5‧‧‧ substrate
3‧‧‧像素電極 3‧‧‧pixel electrode
4‧‧‧ITO電極 4‧‧‧ITO electrodes
6‧‧‧著色圖案 6‧‧‧Coloring pattern
7‧‧‧黑色矩陣 7‧‧‧Black matrix
8‧‧‧保護膜 8‧‧‧Protective film
12‧‧‧配向膜 12‧‧‧Alignment film
13‧‧‧液晶 13‧‧‧LCD
14‧‧‧偏光板 14‧‧‧Polar plate
16‧‧‧密封材料 16‧‧‧ Sealing material
17‧‧‧背光源光 17‧‧‧Backlight light
20‧‧‧彩色濾光片 20‧‧‧Color filters
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