JP2013238859A - Ink composition for inkjet color filter superior in storage stability, and cured film of inkjet color filter and color filter obtained by using ink composition - Google Patents
Ink composition for inkjet color filter superior in storage stability, and cured film of inkjet color filter and color filter obtained by using ink composition Download PDFInfo
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- JP2013238859A JP2013238859A JP2013121750A JP2013121750A JP2013238859A JP 2013238859 A JP2013238859 A JP 2013238859A JP 2013121750 A JP2013121750 A JP 2013121750A JP 2013121750 A JP2013121750 A JP 2013121750A JP 2013238859 A JP2013238859 A JP 2013238859A
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- Prior art keywords
- color filter
- ink composition
- pigment
- component
- acid
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 94
- 238000003860 storage Methods 0.000 title abstract description 8
- 239000000049 pigment Substances 0.000 claims abstract description 64
- 239000002904 solvent Substances 0.000 claims abstract description 39
- 239000002270 dispersing agent Substances 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 26
- 229920005989 resin Polymers 0.000 claims abstract description 22
- 239000011347 resin Substances 0.000 claims abstract description 22
- 239000007787 solid Substances 0.000 claims abstract description 14
- 239000004593 Epoxy Substances 0.000 claims description 22
- -1 acrylate compound Chemical class 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
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- 239000006185 dispersion Substances 0.000 description 61
- 238000012360 testing method Methods 0.000 description 25
- 150000008065 acid anhydrides Chemical class 0.000 description 23
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 20
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 18
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 11
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- 238000000576 coating method Methods 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
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- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 5
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
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- 239000000047 product Substances 0.000 description 3
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- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
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- 125000002723 alicyclic group Chemical group 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
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- 239000003086 colorant Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Optical Filters (AREA)
- Liquid Crystal (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
本発明は、インクジェット法によってカラーフィルターを作製するのに適した貯蔵安定性に優れたカラーフィルター用インキ組成物、並びにこのインキ組成物を用いて得たカラーフィルター硬化膜、及びカラーフィルターに関する。 The present invention relates to an ink composition for a color filter excellent in storage stability suitable for producing a color filter by an inkjet method, a color filter cured film obtained by using this ink composition, and a color filter.
カラー液晶表示装置に使われるカラーフィルターのこれまでの製造方法としては、感光性樹脂に光重合開始剤、各種添加剤、及び赤色(R)、緑色(G)、青色(B)の各着色剤を加えた後、溶剤によって調製したカラーレジストを塗布し乾燥後、一連の工程により画素パターンをフォトリソ法により形成したものが主流である。しかしながら、近時のマザーガラスの大型化に伴い、従来のフォトリソ法によるカラーフィルターの製造方法では、塗布工程などの各工程に於いて技術的な問題点が生じ始めている。 Conventional methods for producing color filters used in color liquid crystal display devices include photopolymerization initiators, various additives, and red (R), green (G), and blue (B) colorants for photosensitive resins. In general, a color resist prepared with a solvent is applied, dried, and then a pixel pattern is formed by a photolithographic method through a series of steps. However, with the recent increase in size of mother glass, technical problems have begun to occur in each process such as the coating process in the conventional color filter manufacturing method using the photolithography method.
例えば、これまでスピンコートを用いた塗工方法が主に用いられているが、ベースとなるマザーガラスが大きくなるにつれ、スピンコートで塗布することは技術的に困難になり、替わりにスリットコータを用いた塗工方法が採用されている。ところが、スリットコータを用いた塗工方法でも更なるマザーガラスの大型化により全面に均一な塗膜を形成することが難しく、特に８Ｇ、１０Ｇクラスといった超大型マザーガラスではこの問題はより一層顕著になる。また、フォトリソ法では３色ごとに塗工、乾燥、露光、現像、硬化の各処理が必要となることから、工程数が嵩みコスト高となってしまうと言う問題もあり、フォトリソ法とは別の画素形成手段が望まれている。 For example, coating methods using spin coating have been mainly used so far, but as the mother glass as the base becomes larger, it becomes technically difficult to apply by spin coating, and instead a slit coater is used. The coating method used is employed. However, even with a coating method using a slit coater, it is difficult to form a uniform coating film on the entire surface due to further enlargement of the mother glass, and this problem becomes even more pronounced with super large mother glasses such as 8G and 10G classes. Become. In addition, since the photolithographic method requires coating, drying, exposure, development, and curing processes for every three colors, there is a problem that the number of steps increases and the cost is high. Another pixel forming means is desired.
そこで、フォトリソ法に替わるカラーフィルターの製造方法として、例えば特許文献１に開示されているようなオフセット印刷法を用いた画像形成が提案され、実施されている。しかしながらオフセット印刷法に関しても十分に超大型マザーガラスに対して安定した画素形成は困難な状態となっており、実用化が遅れている。これに対してインクジェット法による画素形成方法は、近年注目を集め、実施され、ある程度の実績を残していることは周知の事実である。そして、インクジェット法において使用されるインキについて幾つかの特許が提示されている（例えば特許文献２〜４参照）。 Therefore, as a color filter manufacturing method replacing the photolithography method, for example, image formation using an offset printing method as disclosed in Patent Document 1 has been proposed and implemented. However, with respect to the offset printing method, it is difficult to form a stable pixel on a sufficiently large mother glass, and its practical application is delayed. On the other hand, it is a well-known fact that the pixel forming method by the ink jet method has been attracting attention and implemented in recent years and has a certain track record. And several patents are shown about the ink used in the inkjet method (for example, refer patent documents 2-4).
ところで、テレビ用途に耐えうるような良好な画像を液晶表示装置で実現するためには、液晶表示装置そのものや回路に格段の技術向上が求められるが、その中でカラーフィルターがより大きなＮＴＳＣ比、コントラストなど、良好な表示仕様を達成できることも要求の一つである。その為には、カラーフィルター用のインキ組成物により多くの顔料を含有させる必要がある。しかしながら、インキ組成物における顔料の含有量が増加すると、相対的にインクの貯蔵安定性に関して問題が生じやすくなる。特にフォトリソ法に適したインキの場合には、現像性を確保するために限界まで分散材料を低下させ、安定性をある程度犠牲とした組成を選択せざるを得ない。 By the way, in order to realize a good image that can be used for a television application with a liquid crystal display device, a great technical improvement is required for the liquid crystal display device itself and a circuit. Among them, a color filter has a larger NTSC ratio, One of the requirements is to achieve good display specifications such as contrast. For that purpose, it is necessary to contain more pigments in the ink composition for color filters. However, when the pigment content in the ink composition is increased, a problem is relatively likely to occur with respect to the storage stability of the ink. In particular, in the case of an ink suitable for the photolithography method, in order to ensure developability, it is necessary to select a composition that lowers the dispersion material to the limit and sacrifices the stability to some extent.
本発明は、カラーフィルターの製造において、大型化が進むガラス基板に対して画素パターンを形成するのに適していると共に、低コスト化及び量産化が可能なインクジェット法に用いるインキ組成物について、硬化性に優れて、大きなＮＴＳＣ比を達成すべく顔料を高濃度で含有しても粘度安定性に優れ、常温保存でも安定した粘度を保持できるカラーフィルター用インキ組成物、並びにこのインキ組成物を用いて得たカラーフィルター硬化膜及びカラーフィルターを提供することを目的とする。 The present invention is suitable for forming a pixel pattern on a glass substrate whose size is increasing in the manufacture of a color filter, and for curing an ink composition used in an inkjet method capable of reducing cost and mass production. Ink composition for color filter that is excellent in viscosity, has excellent viscosity stability even if it contains a high concentration of pigment to achieve a large NTSC ratio, and can maintain a stable viscosity even at room temperature storage, and this ink composition An object of the present invention is to provide a color filter cured film and a color filter obtained as described above.
本発明者らは、大きなＮＴＳＣ比を達成すべく顔料を高濃度で含有しても、粘度安定性に優れ、常温保存でも安定した粘度を保持できるインキ組成物について鋭意検討した結果、使用する原料の一つである顔料分散液の顔料と分散剤との比率を一定の範囲におさめてインキ組成物とすることで、常温でも粘度が安定し、インクジェットの吐出性に優れたインクジェット法に適したカラーフィルター向けインキ組成物が得られることを見出し、本発明を完成した。 As a result of intensive studies on an ink composition that has excellent viscosity stability and can maintain a stable viscosity even at room temperature storage, the present inventors have used raw materials to be used even if the pigment is contained at a high concentration to achieve a large NTSC ratio. By adjusting the ratio of the pigment to the dispersant in the pigment dispersion, which is one of the above, to an ink composition, the viscosity is stable even at room temperature and suitable for inkjet methods with excellent inkjet ejection properties. The inventors have found that an ink composition for a color filter can be obtained and completed the present invention.
すなわち、本発明は、インクジェット法によりカラーフィルターを作成するために用いられるカラーフィルター用インク組成物において、インク組成物中の、溶剤を除く固体成分中の顔料量と樹脂量との割合（顔料／樹脂量）が２０〜６０ｗｔ％の範囲であり、かつ、顔料量と顔料を分散させる分散剤の量との割合（分散剤／顔料）が４５〜１２０ｗｔ％の範囲であることを特徴とするインクジェットカラーフィルター用インキ組成物である。 That is, the present invention relates to a ratio of a pigment amount and a resin amount in a solid component excluding a solvent in a color filter ink composition used for preparing a color filter by an inkjet method (pigment / Resin amount) is in the range of 20-60 wt%, and the ratio (dispersant / pigment) between the pigment amount and the amount of the dispersant for dispersing the pigment is in the range of 45-120 wt%. It is an ink composition for color filters.
上記インクジェットカラーフィルター用インキ組成物は、下記一般式（１）で表される不飽和化合物（Ａ）、４官能以上の多官能アクリレート化合物（Ｂ）、顔料（Ｄ）、及び溶剤（Ｈ）を含有し、かつ、上記（Ａ）成分と（Ｂ）成分の重量の比率（Ａ）／（Ｂ）が１０／９０〜９０／１０の範囲で配合されていることが本発明における好ましい態様である。
また、上記インクジェットカラーフィルター用インキ組成物には、２官能以上の多官能エポキシ化合物（Ｃ）を、上記（Ａ）成分と（Ｂ）成分の合計〔（Ａ）＋（Ｂ）〕に対して０〜２０重量％添加するのが更に好ましい態様である。 In the ink composition for inkjet color filter, a polyfunctional epoxy compound (C) having two or more functions is added to the sum of the components (A) and (B) [(A) + (B)]. In a more preferred embodiment, 0 to 20% by weight is added.
ここで、分散剤とは、顔料表面に吸着もしくは固着して顔料同士の凝集を阻害する添加剤であり、一般的に分散剤の基本的な構造は、顔料表面に吸着する吸着部と顔料同士の凝集を阻害する立体反発部を有する。通常、吸着部は、顔料表面とは逆の電荷を持った構造を有しており、例えば、顔料表面が酸性処理を施されていた場合、吸着部は、Ｎａ+やアミンやイミノ構造を有している場合が多い。一方、立体反発部は、長鎖の炭化水素鎖、アクリル、エステル、エーテルなどで連結されている。このように一方に電荷を持ち他方に炭化水素構造を有している事から、分散剤は一種の界面活性剤である。このような分散剤として、市販されているものを例示すると、例えばＢＹＫ Ｃｈｅｍｉｅ社のＤｉｓｐｅｒｂｙｋ−１６０、１６１、１６２、１６３、１６４、１６５、１６６、１６９、１８２、１８３、１８４、１８５、２０００、２００１、２０２０、２０５０、２０７０、２１５０」、Ｅｆｋａ ＣＨＥＭＩＣＡＬＳ社「ＥＦＫＡ−４０４６、４０４７、４０４８、４０５０，４０５５、４４００、４４０１、４４０２」、日本ルブリゾール社「ＳＯＬＳＰＥＲＳＥ２４０００ＳＣ、２４０００ＧＲ、３１８４５」、楠本化成株式会社「デイスパロンＤＡ７０３−５０、ＤＡ−７０５、ＤＡ−７２５」、味の素ファインテクノ株式会社「アジスパーＰＢ７１１、８２１、８２２、８２４、８２７」などがあげられる。 Here, the dispersant is an additive that adsorbs or adheres to the pigment surface and inhibits aggregation of the pigments. In general, the basic structure of the dispersant is an adsorbing part that adsorbs on the pigment surface and the pigments. It has a steric repulsion part that inhibits the aggregation of. Usually, the adsorbing part has a structure having a charge opposite to that of the pigment surface. For example, when the pigment surface has been subjected to an acid treatment, the adsorbing part has Na + , amine or imino structure. There are many cases. On the other hand, the three-dimensional repulsion part is connected with a long hydrocarbon chain, acrylic, ester, ether or the like. Thus, the dispersant is a kind of surfactant because it has a charge on one side and a hydrocarbon structure on the other. Examples of such dispersants that are commercially available include BYPER Chemie's Disperbyk-160, 161, 162, 163, 164, 165, 166, 169, 182, 183, 184, 185, 2000, 2001. 2020, 2050, 2070, 2150 ", Efka CHEMICALS" EFKA-4046, 4047, 4048, 4050, 4055, 4400, 4401, 4402 ", Nippon Lubrizol" SOLPERSE24000SC, 24000GR, 31845 ", Enomoto Kasei Co., Ltd. DA703-50, DA-705, DA-725 ", Ajinomoto Fine Techno Co., Ltd." Ajisper PB711, 821, 822, 824, 827 ".
また、顔料（Ｄ）については、有機顔料であってもよく、無機顔料であってもよい。このうち有機顔料としては、例えばアゾレーキ系、不溶性アゾ（PY-150）系、フタロシアニン系（PG-7、PG-36＆PB-15.6）を含むシアニン系、キノフタロン系（PY138）、キナクドリン系、ジオキサジン（PV-23）系、イソインドリノン（PY-139）系、ベリノン系、アントラキノン（PR-177）系、ピロロピロール系（PR-254）、ペリレン系等を挙げることができ、これの１種又は２種以上を併用することもできる。無機顔料としては、例えばミロリブルー、酸化鉄、コバルト系、マンガン系、群青、紺青、コバルトブルー、セルリアンブルー、ピリジアン、エメラルドグリーン、コバルトグリーン等を挙げることができ、これの１種又は２種以上を併用することもできる。これらの顔料については、得られるカラーフィルターの塗膜（画素）の透明性を維持しつつ着色するために、可視光の波長の下限である0.4μｍ以下の平均粒子径に分散されることが好ましく、実用的に平均粒子径範囲が0.01〜0.25μｍであるのが更に好ましい。 The pigment (D) may be an organic pigment or an inorganic pigment. Among these, examples of organic pigments include azo lakes, insoluble azo (PY-150), phthalocyanine (PG-7, PG-36 & PB-15.6) cyanine, quinophthalone (PY138), quinacdrine, dioxazine (PV -23), isoindolinone (PY-139), berylone, anthraquinone (PR-177), pyrrolopyrrole (PR-254), perylene, etc., one or two of these More than one species can be used in combination. Examples of inorganic pigments include miloli blue, iron oxide, cobalt-based, manganese-based, ultramarine blue, bitumen, cobalt blue, cerulean blue, pyridian, emerald green, cobalt green, and the like. It can also be used together. These pigments are preferably dispersed to an average particle diameter of 0.4 μm or less, which is the lower limit of the wavelength of visible light, in order to color while maintaining the transparency of the coating film (pixel) of the obtained color filter. It is more preferable that the average particle diameter range is 0.01 to 0.25 μm practically.
そして、分散剤と溶剤、及び顔料（Ｄ）を用いて所定の方法で分散して、顔料分散液（分散体）を得るようにする。このうち、分散剤量と顔料量との比率（分散剤／顔料）を３５〜１２０ｗｔ％の範囲として、本発明のインクジェットカラーフィルター用インキ組成物を調製する。顔料分散液における分散剤と顔料（Ｄ）の量が、この範囲の比率を逸脱した場合は、良好なインク特性を発揮できない。すなわち、まず、３５ｗｔ％を下回ると常温での保管中に粘度上昇が進行し、冷蔵保存が必要となる。更に低下して２５ｗｔ％を下回ると冷蔵保存でも粘度の安定が保てなくなる。特にインキに調製する時、粘度調整、色特性調整、乾燥特性調整等、必要に応じて変更する組成の変動に対して広範囲で安定するのは顔料に対する分散剤比率が３５ｗｔ％以上の場合である。一方、分散剤比率が１２０ｗｔ％を超えるとインキに調製する時に硬化などの膜形成、機能付与に必要な樹脂やモノマーなどの比率が相対的に減少し、膜物性に於いて十分な信頼性を発揮できない事があり、広範囲で十分な信頼性を発揮できる組成を実現できるのは１２０％ｗｔ以下である。従って、使用する顔料分散液に於ける顔料（Ｄ）と分散剤との比率は３５〜１２０ｗｔ％、より好ましくは４０〜１００ｗｔ％が望ましい。 And it disperse | distributes by a predetermined method using a dispersing agent, a solvent, and a pigment (D), and obtains a pigment dispersion liquid (dispersion). Among these, the ink composition for inkjet color filters of the present invention is prepared by setting the ratio of the amount of dispersant to the amount of pigment (dispersant / pigment) in the range of 35 to 120 wt%. When the amount of the dispersant and the pigment (D) in the pigment dispersion deviates from the ratio within this range, good ink characteristics cannot be exhibited. That is, when the amount is lower than 35 wt%, the viscosity increases during storage at room temperature, and refrigeration is required. If it further decreases and falls below 25 wt%, the viscosity cannot be kept stable even in refrigerated storage. Especially when it is prepared into an ink, it is stable when the ratio of the dispersant to the pigment is 35 wt% or more when the composition changes as necessary, such as viscosity adjustment, color characteristic adjustment, and drying characteristic adjustment. . On the other hand, when the dispersant ratio exceeds 120 wt%, the ratio of resin and monomers necessary for film formation and function addition such as curing is relatively reduced when preparing an ink, and sufficient reliability in film properties is obtained. It is not possible to exhibit it, and it is 120% wt or less that can realize a composition capable of exhibiting sufficient reliability in a wide range. Therefore, the ratio of the pigment (D) and the dispersant in the pigment dispersion to be used is 35 to 120 wt%, more preferably 40 to 100 wt%.
また、本発明におけるインキ組成物は、溶剤を除く固体成分中の顔料量と樹脂量（インキ組成物から溶剤を除いた固体成分量であり顔料分を含む）との割合（顔料／樹脂量）が２０〜６０ｗｔ％、好ましくは４０〜６０ｗｔ％の範囲であるようにする。樹脂量に対する顔料の割合が２０ｗｔ％より少ないと所望の色特性が得られず、反対に６０ｗｔ％を超えると顔料が凝集しやすくなり、インク吐出時にヘッドが閉塞の原因となる。 In addition, the ink composition in the present invention is a ratio (pigment / resin amount) of the amount of pigment in the solid component excluding the solvent and the amount of resin (the amount of the solid component excluding the solvent from the ink composition and including the pigment component). Is in the range of 20 to 60 wt%, preferably 40 to 60 wt%. If the ratio of the pigment to the resin amount is less than 20 wt%, desired color characteristics cannot be obtained. Conversely, if the ratio exceeds 60 wt%, the pigment tends to aggregate, causing the head to be blocked during ink ejection.
また、本発明におけるインキ組成物は、先に述べた一般式（１）で表される不飽和化合物（Ａ）を樹脂の構成成分として含有する。この（Ａ）成分は、ビスフェノール類から誘導される２個のグリシジルエーテル基を有するエポキシ化合物に（メタ）アクリル酸を反応させ、得られたヒドロキシ基を有する化合物に、多塩基酸であるジカルボン酸又はその酸無水物（以下、「ジカルボン酸類」と称することもある）とテトラカルボン酸又はその酸二無水物（以下、「テトラカルボン酸類」と称する場合もある）とのそれぞれ１種以上と反応させて得られたエポキシ（メタ）アクリレート酸付加物である。なお、本明細書において、（メタ）アクリル酸は、アクリル酸、メタクリル酸又は両方を意味する。 Moreover, the ink composition in this invention contains the unsaturated compound (A) represented by General formula (1) mentioned above as a structural component of resin. This component (A) is a polybasic acid dicarboxylic acid obtained by reacting (meth) acrylic acid with an epoxy compound having two glycidyl ether groups derived from bisphenols. Alternatively, it reacts with one or more of each of an acid anhydride thereof (hereinafter also referred to as “dicarboxylic acids”) and tetracarboxylic acid or an acid dianhydride thereof (hereinafter also referred to as “tetracarboxylic acids”). It is an epoxy (meth) acrylate acid adduct obtained. In the present specification, (meth) acrylic acid means acrylic acid, methacrylic acid or both.
また、上記（Ａ）成分については、好ましくは下記一般式（２）で表されるエポキシ化合物から誘導されるのがよい。このエポキシ化合物はビスフェノール類から誘導されるが、ビスフェノール類をグリシジルエーテル化する際に、オリゴマー単位が混入することになるが、一般式（２）におけるｌの平均値が０〜１０の範囲であればインキ組成物としての性能には問題はない。
上記一般式(２)において、Ｒ1、Ｒ2、Ｒ3、Ｒ4及びＡは、一般式(１)と同様の意味を表すが、Ｒ1、Ｒ2、Ｒ3、及びＲ4について好ましくは水素原子であり、Ａについて好ましくは9,9-フルオレニル基であるのがよい。ｌについては０〜１０の整数、好ましくは０又は０〜２の整数であるのがよい。ここで、9,9-フルオレニル基は、下記式一般式(３)で表される基をいう。
本発明において、（A）成分を得る際の上記エポキシ化合物と（メタ）アクリル酸との反応については、エポキシ化合物１モルに対し、約２モルの（メタ）アクリル酸を使用して行うのがよい。この反応で得られる反応物は、後述する一般式（５）で表されるようなエポキシ（メタ）アクリレート化合物である。そして、このエポキシ（メタ）アクリレート化合物分子中のヒドロキシ基にa)ジカルボン酸類及びb)テトラカルボン酸類を反応させ、エポキシ（メタ）アクリレートの酸付加体を得る。 In the present invention, the reaction between the epoxy compound and (meth) acrylic acid in obtaining the component (A) is performed using about 2 moles of (meth) acrylic acid with respect to 1 mole of the epoxy compound. Good. The reaction product obtained by this reaction is an epoxy (meth) acrylate compound represented by the following general formula (5). Then, the hydroxy group in the epoxy (meth) acrylate compound molecule is reacted with a) dicarboxylic acid and b) tetracarboxylic acid to obtain an acid adduct of epoxy (meth) acrylate.
上記a)ジカルボン酸類としては、鎖式炭化水素ジカルボン酸又はその酸無水物や脂環式ジカルボン酸又はその酸無水物、芳香族ジカルボン酸又はその酸無水物等を使用することができる。このうち、鎖式炭化水素ジカルボン酸又はその酸無水物として、例えばコハク酸、アセチルコハク酸、マレイン酸、アジピン酸、イタコン酸、アゼライン酸、シトラリンゴ酸、マロン酸、グルタル酸、クエン酸、酒石酸、オキソグルタル酸、ピメリン酸、セバシン酸、スベリン酸、ジグリコール酸等の化合物を挙げることができ、更には任意の置換基が導入されたジカルボン酸類又はその酸無水物であってもよい。また、脂環式ジカルボン酸又はその酸無水物として、例えばヘキサヒドロフタル酸、シクロブタンジカルボン酸、シクロペンタンジカルボン酸、ノルボルナンジカルボン酸等の化合物を挙げることができ、更には任意の置換基が導入されたジカルボン酸類又はその酸無水物であってもよい。更に、芳香族ジカルボン酸又はその酸無水物として、例えばフタル酸、イソフタル酸等の化合物を挙げることができ、更には任意の置換基が導入されたジカルボン酸類又はその酸無水物であってもよい。 Examples of the a) dicarboxylic acids include chain hydrocarbon dicarboxylic acids or acid anhydrides thereof, alicyclic dicarboxylic acids or acid anhydrides thereof, aromatic dicarboxylic acids or acid anhydrides thereof, and the like. Among these, as the chain hydrocarbon dicarboxylic acid or its acid anhydride, for example, succinic acid, acetyl succinic acid, maleic acid, adipic acid, itaconic acid, azelaic acid, citralmalic acid, malonic acid, glutaric acid, citric acid, tartaric acid, Examples thereof include compounds such as oxoglutaric acid, pimelic acid, sebacic acid, suberic acid, and diglycolic acid, and further dicarboxylic acids into which an arbitrary substituent is introduced or acid anhydrides thereof. Examples of the alicyclic dicarboxylic acid or its acid anhydride include compounds such as hexahydrophthalic acid, cyclobutane dicarboxylic acid, cyclopentane dicarboxylic acid, norbornane dicarboxylic acid, and further, an arbitrary substituent is introduced. Dicarboxylic acids or acid anhydrides thereof may also be used. Furthermore, examples of the aromatic dicarboxylic acid or acid anhydride thereof include compounds such as phthalic acid and isophthalic acid, and further dicarboxylic acids into which an arbitrary substituent is introduced or acid anhydrides thereof may be used. .
また、b)テトラカルボン酸類としては、鎖式炭化水素テトラカルボン酸又はその酸二無水物、脂環式テトラカルボン酸又はその酸二無水物、芳香族多価カルボン酸又はその酸二無水物等を使用することができる。このうち、鎖式炭化水素テトラカルボン酸又はその酸無水物として、例えばブタンテトラカルボン酸、ペンタンテトラカルボン酸、ヘキサンテトラカルボン酸等を挙げることができ、更には置換基が導入されたテトラカルボン酸類又はその酸無水物であってもよい。また、脂環式テトラカルボン酸又はその酸無水物として、例えばシクロブタンテトラカルボン酸、シクロペンタンテトラカルボン酸、シクロヘキサンテトラカルボン酸、シクロへプタンテトラカルボン酸ノルボルナンテトラカルボン酸等を挙げることができ、更には置換基が導入されたテトラカルボン酸類又はその酸無水物であってもよい。更に、芳香族多価カルボン酸又はその酸無水物として、例えばピロメリット酸、ベンゾフェノンテトラカルボン酸、ビフェニルテトラカルボン酸、ビフェニルエーテルテトラカルボン酸又はその酸無水物等を挙げることができ、更には置換基が導入されたテトラカルボン酸類又はその酸無水物であってもよい。 In addition, as b) tetracarboxylic acids, chain hydrocarbon tetracarboxylic acid or its acid dianhydride, alicyclic tetracarboxylic acid or its acid dianhydride, aromatic polycarboxylic acid or its acid dianhydride, etc. Can be used. Among these, examples of the chain hydrocarbon tetracarboxylic acid or its acid anhydride include butanetetracarboxylic acid, pentanetetracarboxylic acid, hexanetetracarboxylic acid, and the like, and tetracarboxylic acids into which a substituent is further introduced. Or its acid anhydride may be sufficient. Examples of the alicyclic tetracarboxylic acid or its acid anhydride include cyclobutanetetracarboxylic acid, cyclopentanetetracarboxylic acid, cyclohexanetetracarboxylic acid, cycloheptanetetracarboxylic acid norbornanetetracarboxylic acid, and the like. May be a tetracarboxylic acid having a substituent introduced therein or an acid anhydride thereof. Furthermore, examples of the aromatic polyvalent carboxylic acid or acid anhydride thereof include pyromellitic acid, benzophenone tetracarboxylic acid, biphenyl tetracarboxylic acid, biphenyl ether tetracarboxylic acid or acid anhydride thereof, and further substitution. It may be a tetracarboxylic acid having an introduced group or an acid anhydride thereof.
上記a)ジカルボン酸類とb)テトラカルボン酸類については、それぞれ1種以上を使用することができ、a)ジカルボン酸類とb)テトラカルボン酸類の使用割合としてはa/bのモル比で０．１〜１０、好ましくは０．２〜１．０の範囲となるようにするのがよい。この使用割合については、（Ｂ）成分の最適分子量、硬化性、光透過性、耐熱性、対溶剤性などを考慮し適した割合を選択することができる。 As for the above a) dicarboxylic acids and b) tetracarboxylic acids, one or more can be used, respectively, and the use ratio of a) dicarboxylic acids and b) tetracarboxylic acids is 0.1 by a molar ratio of a / b. 10 to 10 and preferably 0.2 to 1.0. As for this use ratio, an appropriate ratio can be selected in consideration of the optimum molecular weight, curability, light transmittance, heat resistance, solvent resistance and the like of the component (B).
また、（Ａ）成分を得る際の上記エポキシ（メタ）アクリレート化合物とa)ジカルボン酸類及びb)テトラカルボン酸類を反応させるには、公知の方法を採用することができるが、好ましくはエポキシ（メタ）アクリレート化合物分子中のヒドロキシ基１モル当たり酸成分が３／４モルとなるように定量的に反応させるのがよい。また、反応温度としては９０〜１３０℃、好ましくは９５〜１２５℃である。 Moreover, in order to make the said epoxy (meth) acrylate compound at the time of obtaining (A) component react with a) dicarboxylic acid and b) tetracarboxylic acid, a well-known method can be employ | adopted, However, Preferably epoxy (meta) is used. ) It is preferable to carry out the reaction quantitatively so that the acid component is 3/4 mol per 1 mol of hydroxy group in the acrylate compound molecule. The reaction temperature is 90 to 130 ° C, preferably 95 to 125 ° C.
（Ａ）成分を製造する方法の一例を9,9-ビス（4-ヒドロキシフェニル）フルオレンを出発原料とする場合について示せば、次のようである。
先ず、9,9-ビス（4-ヒドロキシフェニル）フルオレンとエピクロロヒドリンとを反応させて下記一般式（４）で表されるビスフェノールフルオレン型エポキシ化合物を合成し、このビスフェノールフルオレン型エポキシ化合物とCH2＝CR5-COOHで表される（メタ）アクリル酸とを反応させて下記一般式（５）で表されるビスフェノールフルオレン型エポキシアクリレート樹脂を合成し、次いでプロピレングリコールモノメチル溶剤中でビスフェノールフルオレン型エポキシアクリレート樹脂と上記酸成分とを加熱下に反応させ、（Ａ）成分である前記式（１）で表されるフルオレン型のアルカリ可溶性樹脂を得ることができる。
First, 9,9-bis (4-hydroxyphenyl) fluorene and epichlorohydrin are reacted to synthesize a bisphenolfluorene type epoxy compound represented by the following general formula (4). A bisphenolfluorene type epoxy acrylate resin represented by the following general formula (5) is synthesized by reacting with (meth) acrylic acid represented by CH 2 = CR 5 -COOH, and then bisphenolfluorene in a propylene glycol monomethyl solvent. A fluorene type alkali-soluble resin represented by the above formula (1), which is the component (A), can be obtained by reacting the epoxy acrylate resin with the acid component under heating.
一方、（Ｂ）成分の多官能アクリレート化合物としては、例えば、ジトリメチロールプロパンテトラ(メタ)アクリレート、などのメチロールプロパンで4官能以上のアクリレートやペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、ペンタエリスリトールやジペンタエリスリトールのような骨格で4官能以上のアクリレートや、ペンタアクレレートエステル等のアクリル酸エステル類等を挙げることができる。これらはその1種のみを単独で用いてもよく、また、２種以上を併用することもできる。更には、これらのアクリレートはモノマーであってもよくオリゴマーであってもよい。なお、上記アクリレート構造に関しては、同様の構造に於いても３官能以下を除外すると同時に上記構造以外でも４官能以上であればよく、アクリレートの主骨格に影響されない。 On the other hand, as the polyfunctional acrylate compound of component (B), for example, methylolpropane such as ditrimethylolpropane tetra (meth) acrylate, tetrafunctional or higher acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) ) Acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, skeletons such as pentaerythritol and dipentaerythritol, tetra- or higher functional acrylate, acrylic esters such as pentaacrylate ester, etc. Can be mentioned. These may be used alone or in combination of two or more. Furthermore, these acrylates may be monomers or oligomers. In addition, regarding the acrylate structure described above, the trifunctional or lower functional group is excluded even in the same structure, and at the same time, the functional group may be tetrafunctional or higher other than the above structure, and is not affected by the main skeleton of the acrylate.
本発明において上記（Ａ）成分と（Ｂ）成分の重量の比（Ａ）／（Ｂ）については１０／９０〜９０／１０、好ましくは７０／３０〜４０／６０である。（Ａ）／（Ｂ）が１０／９０〜９０／１０の範囲から外れると、インキ組成物が十分に硬化しなかったり、得られた硬化膜の光透過性が低下してしまい、液晶の発色性に影響を及ぼしたり液晶の電圧保持率が低下するおそれがある。ここで、(Ａ)成分の重量平均分子量(Ｍｗ)は２０００〜２００００の範囲であるのがよい。 In the present invention, the weight ratio (A) / (B) of the component (A) to the component (B) is 10/90 to 90/10, preferably 70/30 to 40/60. When (A) / (B) is out of the range of 10/90 to 90/10, the ink composition is not sufficiently cured, or the light transmittance of the obtained cured film is lowered, and the liquid crystal is colored. The liquid crystal voltage holding ratio may be reduced. Here, the weight average molecular weight (Mw) of the component (A) is preferably in the range of 2000 to 20000.
本発明においては、２官能以上の多官能エポキシ化合物（Ｃ）を（Ａ）成分及び（Ｂ）成分の和に対して２０重量％以下含有するようにしてもよい。ここで、多官能エポキシ化合物（Ｃ）は、一分子中に２以上のエポキシ基を有するエポキシ化合物からなる。例えばフェノールノボラック型エポキシ、クレゾールノボラック型エポキシなどのノボラック型エポキシ樹脂、ビスフェノールＡ型エポキシ、ビスフェノールＦ型エポキシなどのビス型エポキシ樹脂やビフェニル型エポキシ樹脂、脂環式エポキシ樹脂等を代表的なものとして例示することができる。つまり、本発明における多官能エポキシ化合物（Ｃ）は、最大２０重量％を限度とし、最小は０重量％でもよい。 In this invention, you may make it contain 20 weight% or less of polyfunctional epoxy compounds (C) more than bifunctional with respect to the sum of (A) component and (B) component. Here, the polyfunctional epoxy compound (C) is composed of an epoxy compound having two or more epoxy groups in one molecule. Typical examples include novolak epoxy resins such as phenol novolac type epoxy and cresol novolak type epoxy, bis type epoxy resins such as bisphenol A type epoxy and bisphenol F type epoxy, biphenyl type epoxy resins, and alicyclic epoxy resins. It can be illustrated. That is, the polyfunctional epoxy compound (C) in the present invention may have a maximum of 20% by weight and a minimum of 0% by weight.
本発明のカラーフィルター用インキ組成物は、前記(Ａ)、(Ｂ)及び(Ｄ)成分のほか、必要に応じて添加される（Ｃ）成分を溶剤（Ｈ）に溶解又は分散してなる。溶剤としては、メチルエチルケトン、シクロヘキサノン、メチルシクロヘキサノン等のケトン類、メチルセロソルブ、エチルセロソルブ、セロソルブアセテート等のセロソルブ類、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールn-プロピルエーテル、プロピレングリコールn-ブチルエーテル等のプロピレングリコールモノアルキルエーテル類、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールn-プロピルエーテルアセテート、プロピレングリコールn-ブチルエーテルアセテート等のプロピレングリコールモノアルキルエーテルアセテート類、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールジブチルエーテル等のジエチレングリコールジアルキルエーテル類、乳酸メチル、乳酸エチル等の乳酸エステル類、酢酸n-ブチル等の酢酸エステル類の他、γ−ブチロラクトン、Ｎ−メチルピロリドン、ジメチルスルホキシド等の有機溶剤を例示することができる。 The ink composition for a color filter of the present invention is obtained by dissolving or dispersing the component (C) added as necessary in addition to the components (A), (B) and (D) in the solvent (H). . Solvents include ketones such as methyl ethyl ketone, cyclohexanone, methylcyclohexanone, cellosolves such as methyl cellosolve, ethyl cellosolve, cellosolve acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol n-propyl ether, propylene glycol n- Propylene glycol monoalkyl ethers such as butyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol n-propyl ether acetate, propylene glycol monoalkyl ether acetates such as propylene glycol n-butyl ether acetate, diethylene glycol dimethyl ether, Diethylene In addition to diethylene glycol dialkyl ethers such as recall diethyl ether and diethylene glycol dibutyl ether, lactate esters such as methyl lactate and ethyl lactate, acetate esters such as n-butyl acetate, γ-butyrolactone, N-methylpyrrolidone, dimethyl sulfoxide, etc. An organic solvent can be illustrated.
本発明においては、好ましくはこれら有機溶剤を２種以上使用した混合溶剤とするのがよい。この場合、使用される溶剤の沸点がいずれも１２０〜３５０℃の範囲であるのが更に好ましい。 In the present invention, a mixed solvent using two or more of these organic solvents is preferable. In this case, it is more preferable that the solvent used has a boiling point in the range of 120 to 350 ° C.
また、（Ｂ）成分を使用する場合には、光重合開始剤（Ｆ）として、アセトフェノン、p-tert-ブチルアセトフェノン等のアセトフェノン類、ベンゾフェノン、2-クロロベンゾフェノン、p,p'-ビス(ジメチルアミノ)ベンゾフェノン等のベンゾフェノン類、ベンゾインメチルエーテル、ベンゾインイソプロピルエーテル、ベンゾインブチルエーテル等のベンゾインエーテル類、2-メチル-1 [4-(メチルチオ)フェニル]-2-モルフォリノプロパン-1-オン、2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタノン-1等のα-アミノアルキルフェノン類、ビス(2,4,6-トリメチルベンゾイル)-フェニル-ホスファイン-オキサイド等のビスアシルフォスフィンオキサイド類、N-フェニルグリシン等のグリシン類、2,4-トリクロロメチル-(ピぺロニル)-6-トリアジン、2,4-トリクロロメチル-(4'-メトキシスチリル)-6-トリアジン等のトリアジン類等を添加するのがよい。これらは単独で用いてもよく、２種以上を併用してもよい。また、この光重合開始剤（Ｆ）は、p-ジメチルアミノ安息香酸イソアミルエステル、p-ジメチルアミノ安息香酸エチルエステル等の公知の光重合促進剤（増感剤）と併用することもできる。（Ｆ）成分の使用量については、（Ｂ）成分と（Ａ）成分の総量１００重量部に対して０．１〜２０重量部であることが好ましい。 In addition, when the component (B) is used, the photopolymerization initiator (F) includes acetophenones such as acetophenone and p-tert-butylacetophenone, benzophenone, 2-chlorobenzophenone, p, p'-bis (dimethyl). Benzophenones such as amino) benzophenone, benzoin ethers such as benzoin methyl ether, benzoin isopropyl ether and benzoin butyl ether, 2-methyl-1 [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2- Α-Aminoalkylphenones such as benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, bis such as bis (2,4,6-trimethylbenzoyl) -phenyl-phosphine-oxide Acylphosphine oxides, glycines such as N-phenylglycine, 2,4-trichloromethyl- (piperonyl) -6-triazine, 2,4- Rikuroromechiru - (4'-methoxy styryl) it is preferable to add a 6-triazine triazines such like. These may be used alone or in combination of two or more. The photopolymerization initiator (F) can also be used in combination with known photopolymerization accelerators (sensitizers) such as p-dimethylaminobenzoic acid isoamyl ester and p-dimethylaminobenzoic acid ethyl ester. About the usage-amount of (F) component, it is preferable that it is 0.1-20 weight part with respect to 100 weight part of total amounts of (B) component and (A) component.
更に、本発明では、カラーフィルター用インキ組成物の他の性能を阻害しない範囲であれば、インクジェット適正を調節する目的から粘度調整剤（Ｇ）を添加することもできる。粘度調整剤（Ｇ）には、粘度を低下させるものと、粘度を高くするものとがある。粘度を低下させるものには、一般的には、溶剤もこれに含まれるが、本発明では通常の溶剤は粘度調整剤ではなく溶剤と看做し、低分子の官能基を有する反応性希釈剤を粘度調整剤（Ｇ）とする。一方、粘度を高くするものには、シリカ粒子を分散させたシリカ系エアロジェルや、アマイド系ワックス、ベントナイト系の増粘剤がある。これらを必要に応じて添加する事で粘度調整を実施する。 Furthermore, in this invention, if it is a range which does not inhibit the other performance of the ink composition for color filters, a viscosity modifier (G) can also be added from the objective of adjusting an inkjet suitability. The viscosity modifier (G) includes those that lower the viscosity and those that increase the viscosity. In general, a solvent for reducing the viscosity includes a solvent, but in the present invention, a normal solvent is regarded as a solvent, not a viscosity modifier, and a reactive diluent having a low molecular functional group. Is a viscosity modifier (G). On the other hand, those that increase the viscosity include silica airgel in which silica particles are dispersed, amide wax, and bentonite thickener. Viscosity adjustment is performed by adding these as needed.
更にまた、本発明のカラーフィルター用インキ組成物は、本発明の効果を損なわない範囲であれば、他の成分を含有してもよい。例えば、濡れ性を向上させるためには界面活性剤が使用されてもよく、密着性向上のためにはカップリング剤が好ましく使用される。この場合、界面活性剤は0.01〜0.2wt％の範囲で含有させることが好ましい。 Furthermore, the color filter ink composition of the present invention may contain other components as long as the effects of the present invention are not impaired. For example, a surfactant may be used to improve wettability, and a coupling agent is preferably used to improve adhesion. In this case, the surfactant is preferably contained in the range of 0.01 to 0.2 wt%.
本発明におけるインキ組成物については、インクジェット法によりガラス基板等の所定の領域に塗布した後、例えば５０〜１３０℃で１〜１０分の乾燥処理を施し、次いで２００〜２６０℃で０．５〜２時間の熱硬化を行うことで所定の画像を形成することができる。この際のインクジェット法としては、一般に用いられる手段を採用することができ、例えば所定のブラックマトリックスパターン形状の凹部にインキ組成物を吐出、塗布し、乾燥、硬化してもよい。 About the ink composition in this invention, after apply | coating to the predetermined | prescribed area | regions, such as a glass substrate, by the inkjet method, for example, the drying process is performed for 1 to 10 minutes at 50-130 degreeC, and then 0.5-200 at 200-260 degreeC. A predetermined image can be formed by performing thermosetting for 2 hours. As the ink jet method at this time, generally used means may be employed. For example, the ink composition may be discharged, applied, dried and cured in a recess having a predetermined black matrix pattern shape.
本発明のインクジェット用インキ組成物は、大型化が進むガラス基板に対して画素パターンを形成するのに適していると共に、低コスト化及び量産化が可能なインクジェット法に用いるインキ組成物である。本発明のインキ組成物は、このようにインクジェット特性を維持しつ、常温で安定な粘度を維持しながら電圧保持率などの信頼性を確保できるインクジェットカラーフィルター用インキ材料である。 The ink-jet ink composition of the present invention is an ink composition used for an ink-jet method that is suitable for forming a pixel pattern on a glass substrate that is increasing in size, and that can be reduced in cost and mass-produced. The ink composition of the present invention is an ink material for an ink jet color filter that can maintain reliability such as voltage holding ratio while maintaining a stable viscosity at room temperature while maintaining ink jet characteristics as described above.
以下、実施例により本発明を更に詳しく説明するが、本発明はこれに限定されるものではない。なお、実施例中、別段の断りがない限り、部は重量部を表し、%は重量%を表す。 EXAMPLES Hereinafter, although an Example demonstrates this invention in more detail, this invention is not limited to this. In the examples, unless otherwise specified, parts represent parts by weight and% represents% by weight.
［Blue分散体Ａ（顔料分散液）処方例］
顔料PB;15.6（100g）を２Ｌのステンレス容器に採取し、あらかじめブチルカルビトールアセテート５０％溶液としていたＰＢ８２４（味の素社製 分散剤）を61g加えた。これをセラミックコーティングを施した3本ロールにて流動性が出るまで混練する。この混練品に更にブチルカルビトールアセテート130g添加、混合した後、横型サンドミルにて分散し、顔料の平均粒径が100nm以下になるまで分散した。分散完了後、ブチルカルビトールアセテート（400g）で希釈して固形分が１９％とし試験用分散液とした。
[Blue dispersion A (pigment dispersion) formulation example]
Pigment PB; 15.6 (100 g) was collected in a 2 L stainless steel container, and 61 g of PB824 (dispersant manufactured by Ajinomoto Co., Inc.), which had been made into a 50% butyl carbitol acetate solution in advance, was added. This is kneaded with three rolls coated with ceramic coating until fluidity comes out. To this kneaded product, 130 g of butyl carbitol acetate was further added and mixed, and then dispersed with a horizontal sand mill until the average particle size of the pigment was 100 nm or less. After the dispersion was completed, the dispersion was diluted with butyl carbitol acetate (400 g) to a solid content of 19%, and a test dispersion was obtained.
［Blue分散体Ｂ（顔料分散液）処方例］
顔料PB;15.6（100g）を２Ｌのステンレス容器に採取し、あらかじめブチルカルビトールアセテート５０％溶液としていたＰＢ８２４（味の素社製 分散剤）を107g加え、後に添加するブチルカルビトールアセテートを168gとした以外はBlue分散体Ａ処方と同様に処理した。分散完了後、ブチルカルビトールアセテート（400g）で希釈して固形分が20％とし試験用分散液とした。
[Blue dispersion B (pigment dispersion) formulation example]
Pigment PB; 15.6 (100 g) was collected in a 2 L stainless steel container, 107 g of PB824 (dispersant manufactured by Ajinomoto Co., Inc.), which had been made into a 50% butyl carbitol acetate solution in advance, was added, and butyl carbitol acetate added later was changed to 168 g. Was processed in the same manner as the Blue Dispersion A formulation. After the dispersion was completed, the dispersion was diluted with butyl carbitol acetate (400 g) to a solid content of 20%, and a test dispersion was obtained.
［Red分散体Ａ（顔料分散液）処方例］
顔料PR254とPY150を80／20に混合したもの100gを２Ｌのステンレス容器に採取し、Ｄｉｓｐｅｒｂｙｋ−２０００（ＢＹＫ Ｃｈｅｍｉｅ社製 分散剤）を75.5g加えた。これをセラミックコーティングを施した3本ロールにて流動性が出るまで混練した。更にブチルカルビトールアセテート200g添加、混合した後、混練品を横型サンドミルにて分散し、顔料の平均粒径が100nm以下になるまで分散した。分散完了後、ブチルカルビトールアセテート（400g）で希釈して固形分が１７％とし試験用分散液とした。
[Red dispersion A (pigment dispersion) formulation example]
100 g of a mixture of pigments PR254 and PY150 in 80/20 was collected in a 2 L stainless steel container, and 75.5 g of Disperbyk-2000 (a dispersing agent manufactured by BYK Chemie) was added. This was kneaded with a three roll coated with ceramic coating until fluidity appeared. Further, 200 g of butyl carbitol acetate was added and mixed, and then the kneaded product was dispersed with a horizontal sand mill until the average particle size of the pigment was 100 nm or less. After the dispersion was completed, the dispersion was diluted with butyl carbitol acetate (400 g) to a solid content of 17%, and a test dispersion was obtained.
［Red分散体Ｂ（顔料分散液）処方例］
顔料PR254とPY150を80／20に混合したもの100gを２Ｌのステンレス容器に採取し、Ｄｉｓｐｅｒｂｙｋ−２０００（ＢＹＫ Ｃｈｅｍｉｅ社製 分散剤）を148g加え、後に添加するブチルカルビトールアセテートを105gとした以外はRed 分散体Ａ処方と同様に処理した。分散完了後、ブチルカルビトールアセテート（400g）で希釈して固形分が２３％とし試験用分散液とした。
[Prescription Example of Red Dispersion B (Pigment Dispersion)]
100g of pigment PR254 and PY150 mixed in 80/20 was collected in a 2L stainless steel container, Disperbyk-2000 (dispersant manufactured by BYK Chemie) was added, and butyl carbitol acetate added later was changed to 105g. Treated as for Red Dispersion A formulation. After completion of dispersion, the dispersion was diluted with butyl carbitol acetate (400 g) to a solid content of 23%, and a test dispersion was obtained.
［Green分散体Ａ（顔料分散液）処方例］
顔料PG36とPY150を60／40に混合したもの100gを２Ｌのステンレス容器に採取し、あらかじめジエチレングリコールブチルエーテルアセテート(別称：ブチルカルビトールアセテート(以後BCA))５０％溶液としていたＰＢ８２７(味の素社製 分散剤)を60g加えた。これをセラミックコーティングを施した3本ロールにて流動性が出るまで混練した。更にBCA（107g）を添加、混合した後、混練品を横型サンドミルにて分散し、顔料の平均粒径が100nm以下になるまで分散した。分散完了後、BCA（400g）で希釈して固形分が２０％とし試験用分散液とした。
[Green dispersion A (pigment dispersion) formulation example]
100g of pigment PG36 and PY150 mixed in 60/40 was collected in a 2L stainless steel container and PB827 (dispersed by Ajinomoto Co., Inc.) previously made into a 50% solution of diethylene glycol butyl ether acetate (also known as butyl carbitol acetate (hereinafter BCA)). 60 g) was added. This was kneaded with a three roll coated with ceramic coating until fluidity appeared. Further, BCA (107 g) was added and mixed, and then the kneaded product was dispersed with a horizontal sand mill until the average particle size of the pigment was 100 nm or less. After the dispersion was completed, the dispersion was diluted with BCA (400 g) to give a solid content of 20% to obtain a test dispersion.
［Green分散体Ｂ（顔料分散液）処方例］
顔料PG36とPY150を60／40に混合したもの100gを２Ｌのステンレス容器に採取し、あらかじめBCA５０％溶液としていたＰＢ８２７（味の素社製 分散剤）を91g加え、後に添加するBCAを141gとした以外はGreen分散体Ａ処方と同様に処理した。分散完了後、BCA（300g）で希釈して固形分が２３％とし試験用分散液とした。
[Green dispersion B (pigment dispersion) formulation example]
100g of pigment PG36 and PY150 mixed in 60/40 was collected in a 2L stainless steel container, 91g of PB827 (dispersant made by Ajinomoto Co., Inc.) previously made into BCA 50% solution was added, and BCA added later was 141g. Treated as for Green Dispersion A formulation. After the dispersion was completed, the dispersion was diluted with BCA (300 g) to a solid content of 23%, and a test dispersion was obtained.
［Green分散体Ｃ（顔料分散液）処方例］
顔料PG36とPY150を60／40に混合したもの100gを２Ｌのステンレス容器に採取し、あらかじめBCA５０％溶液としていたＰＢ８２７（味の素社製 分散剤）を200g加え、後に添加するBCAを350gとした以外はGreen分散体Ａ処方と同様に処理した。分散完了後、BCA（350g）で希釈して固形分が３０％とし試験用分散液とした。
[Green dispersion C (pigment dispersion) formulation example]
100g of pigment PG36 and PY150 mixed in 60/40 was collected in a 2L stainless steel container, 200g of PB827 (dispersant made by Ajinomoto Co., Inc.) previously made into 50% BCA solution was added, and BCA added later was 350g. Treated as for Green Dispersion A formulation. After the dispersion was completed, the dispersion was diluted with BCA (350 g) to give a solid content of 30% to obtain a test dispersion.
［Green分散体D（顔料分散液）処方例］
顔料PG36とPY150を60／40に混合したもの100gを２Ｌのステンレス容器に採取し、あらかじめBCA５０％溶液としていたＰＢ８２７（味の素社製 分散剤）を266g加え、後に添加するBCAを204gとした以外はGreen分散体Ａ処方と同様に処理した。分散完了後、BCA（400g）で希釈して固形分が２４％とし試験用分散液とした。
[Green dispersion D (pigment dispersion) formulation example]
100g of pigment PG36 and PY150 mixed in 60/40 was collected in a 2L stainless steel container, except that 266g of PB827 (dispersant made by Ajinomoto Co., Inc.) previously made into BCA 50% solution was added, and BCA added later was 204g. Treated as for Green Dispersion A formulation. After the dispersion was completed, the dispersion was diluted with BCA (400 g) to give a solid content of 24% to obtain a test dispersion.
すべての分散体に関しては、調製後に約1gを採取した後、160℃で2時間乾燥後、初期重量との差から計算した固形分を基にして計算した組成比を表1に示す。 For all the dispersions, about 1 g was collected after preparation, dried at 160 ° C. for 2 hours, and the composition ratio calculated based on the solid content calculated from the difference from the initial weight is shown in Table 1.
［実施例１］
ビーカー（1000ml）に回転子を入れ、マグネチックスターラーに設置した。溶剤としてBCA 210.5gを秤量し、攪拌しながら（Ｃ）成分としてYX4000HK (ジャパンエポキシレジン社製)を4.0g加えた。これらの溶解を確認した後、（Ａ）成分のフルオレン型エポキシ型アクリレート／酸無水物重合付加体のPGMEA(プロピレングリコールモノメチルエーテルアセテート)溶液（新日鐵化学(株)製 Ｖ259ME 樹脂成分等56.5％）を42.5gと（Ｂ）成分のジペンタエリスリトールヘキサアクリレートDPHA（日本化薬社製）16.0ｇとを添加して、攪拌した。次に、あらかじめ分散、調製した（Ｄ）成分、分散剤及び溶剤からなるGreen分散体Ｂを227.0g加えて更に攪拌した。最後に添加剤のシランカップリング剤と界面活性剤を各2.5gと0.3g添加した後、さらに30分攪拌して試験用インキ組成物を得た。組成及び後述する評価結果を表２に示す。
[Example 1]
The rotor was placed in a beaker (1000 ml) and placed on a magnetic stirrer. 210.5 g of BCA was weighed as a solvent, and 4.0 g of YX4000HK (manufactured by Japan Epoxy Resin Co., Ltd.) was added as component (C) while stirring. After confirming their dissolution, PGMEA (propylene glycol monomethyl ether acetate) solution of (A) component fluorene type epoxy acrylate / acid anhydride polymerization adduct (V259ME resin component made by Nippon Steel Chemical Co., Ltd.) 56.5% 42.5 g and (B) component dipentaerythritol hexaacrylate DPHA (manufactured by Nippon Kayaku Co., Ltd.) 16.0 g were added and stirred. Next, 227.0 g of Green dispersion B composed of component (D), a dispersant and a solvent, which were previously dispersed and prepared, was added and further stirred. Finally, 2.5 g and 0.3 g of the additive silane coupling agent and surfactant were added, and the mixture was further stirred for 30 minutes to obtain a test ink composition. Table 2 shows the composition and evaluation results described below.
［実施例２］
ビーカー（1000ml）に回転子を入れ、マグネチックスターラーに設置した。溶剤としてBCA 133.7gを秤量し、攪拌しながら（Ｃ）成分としてYX4000HK (ジャパンエポキシレジン社製)を2.4g加えた。これらの溶解を確認した後、（Ａ）成分のフルオレン型エポキシ型アクリレート／酸無水物重合付加体のPGMEA溶液（新日鐵化学(株)製 Ｖ259ME 樹脂成分等56.5％）を24.7gと（Ｂ）成分のジペンタエリスリトールヘキサアクリレートDPHA（日本化薬社製）9.3ｇとを添加して、攪拌した。次に、あらかじめ分散、調製した（Ｄ）成分、分散剤及び溶剤からなるGreen分散体Ｂを330.0g加えて更に攪拌した。最後に添加剤のシランカップリング剤と界面活性剤を各2.5gと0.3g添加した後、さらに30分攪拌して試験用インキ組成物を得た。組成及び評価結果を表２に示す。
[Example 2]
The rotor was placed in a beaker (1000 ml) and placed on a magnetic stirrer. 133.7 g of BCA was weighed as a solvent, and 2.4 g of YX4000HK (manufactured by Japan Epoxy Resin Co., Ltd.) was added as component (C) while stirring. After confirming these dissolutions, 24.7 g of PGMEA solution (5259% V259ME resin component, etc., manufactured by Nippon Steel Chemical Co., Ltd.) of (A) component fluorene type epoxy acrylate / anhydride polymer adduct ) Component dipentaerythritol hexaacrylate DPHA (manufactured by Nippon Kayaku Co., Ltd.) 9.3 g was added and stirred. Next, 330.0 g of Green dispersion B composed of component (D), a dispersant and a solvent, which had been dispersed and prepared in advance, was added and further stirred. Finally, 2.5 g and 0.3 g of the additive silane coupling agent and surfactant were added, and the mixture was further stirred for 30 minutes to obtain a test ink composition. The composition and evaluation results are shown in Table 2.
［実施例３］
ビーカー（1000ml）に回転子を入れ、マグネチックスターラーに設置した。溶剤としてBCA 139.65gを秤量し、攪拌しながら、（A）成分のフルオレン型エポキシ型アクリレート／酸無水物重合付加体のPGMEA溶液（新日鐵化学(株)製 Ｖ259ME 樹脂成分等56.5％）を38.0gと（Ｂ）成分のジペンタエリスリトールヘキサアクリレートDPHA（日本化薬社製）14.5ｇとを添加して、攪拌した。次に、あらかじめ分散、調製した（Ｄ）成分、分散剤及び溶剤からなるBlue分散体Ｂを307.9g加えて更に攪拌した。最後に添加剤のシランカップリング剤と界面活性剤を各2.5gと0.3g添加した後、さらに30分攪拌して試験用インキ組成物を得た。組成及び評価結果を表２に示す。
[Example 3]
The rotor was placed in a beaker (1000 ml) and placed on a magnetic stirrer. Weigh 139.65g of BCA as a solvent and stir, while stirring, add PGMEA solution of component (A) fluorene type epoxy acrylate / acid anhydride polymerization adduct (V259ME resin component etc. made by Nippon Steel Chemical Co., Ltd. 56.5%) 38.0 g and 14.5 g of (B) component dipentaerythritol hexaacrylate DPHA (manufactured by Nippon Kayaku Co., Ltd.) were added and stirred. Next, 307.9 g of Blue Dispersion B composed of component (D), a dispersant and a solvent previously dispersed and prepared was added and further stirred. Finally, 2.5 g and 0.3 g of the additive silane coupling agent and surfactant were added, and the mixture was further stirred for 30 minutes to obtain a test ink composition. The composition and evaluation results are shown in Table 2.
［実施例４］
ビーカー（1000ml）に回転子を入れ、マグネチックスターラーに設置した。溶剤としてBCA 368.0gを秤量し、攪拌しながら（Ｃ）成分としてYX4000HK (ジャパンエポキシレジン社製)を2.5g加えた。これらの溶解を確認した後、（Ａ）成分のフルオレン型エポキシ型アクリレート／酸無水物重合付加体のPGMEA溶液（新日鐵化学(株)製 Ｖ259ME 樹脂成分等56.5％）を26.0gと（Ｂ）成分のジペンタエリスリトールヘキサアクリレートDPHA（日本化薬社製）10.0ｇとを添加して、攪拌した。次に、あらかじめ分散、調製した（Ｄ）成分、分散剤及び溶剤からなるRed分散体Ｂを284.0g加えて更に攪拌した。最後に添加剤のシランカップリング剤と界面活性剤を各2.5gと0.3g添加した後、さらに30分攪拌して試験用インキ組成物を得た。組成及び評価結果を表２に示す。
[Example 4]
The rotor was placed in a beaker (1000 ml) and placed on a magnetic stirrer. BCA 368.0 g was weighed as a solvent, and 2.5 g of YX4000HK (manufactured by Japan Epoxy Resin Co., Ltd.) was added as component (C) while stirring. After confirming their dissolution, 26.0 g of PGMEA solution (5259% V259ME resin component, etc., manufactured by Nippon Steel Chemical Co., Ltd.) of (A) component fluorene type epoxy acrylate / acid anhydride polymerization adduct (B) ) Component dipentaerythritol hexaacrylate DPHA (manufactured by Nippon Kayaku Co., Ltd.) 10.0 g was added and stirred. Next, 284.0 g of Red dispersion B composed of component (D), a dispersant and a solvent, which were previously dispersed and prepared, was added and further stirred. Finally, 2.5 g and 0.3 g of the additive silane coupling agent and surfactant were added, and the mixture was further stirred for 30 minutes to obtain a test ink composition. The composition and evaluation results are shown in Table 2.
［実施例５］
ビーカー（1000ml）に回転子を入れ、マグネチックスターラーに設置した。溶剤としてBCAを222.7g秤量し、攪拌しながら（Ｃ）成分としてYX4000HK (ジャパンエポキシレジン社製)を1.3g加えた。これらの溶解を確認した後、（Ａ）成分のフルオレン型エポキシ型アクリレート／酸無水物重合付加体のPGMEA溶液（新日鐵化学(株)製 Ｖ259ME 樹脂成分等56.5％）を12.7gと（Ｂ）成分のジペンタエリスリトールヘキサアクリレートDPHA（日本化薬社製）4.8ｇとを添加して、攪拌した。次に、あらかじめ分散、調製した（Ｄ）成分、分散剤及び溶剤からなるGreen分散体Ｃを351.5g加えて更に攪拌した。最後に添加剤のシランカップリング剤と界面活性剤を各3.0gと0.3g添加した後、さらに30分攪拌して試験用インキ組成物を得た。組成及び評価結果を表２に示す。
[Example 5]
The rotor was placed in a beaker (1000 ml) and placed on a magnetic stirrer. 222.7 g of BCA was weighed as a solvent, and 1.3 g of YX4000HK (manufactured by Japan Epoxy Resin Co., Ltd.) was added as component (C) while stirring. After confirming their dissolution, 12.7 g of PGMEA solution (5259% V259ME resin component, etc. manufactured by Nippon Steel Chemical Co., Ltd.) of (A) component fluorene type epoxy acrylate / anhydride polymer adduct ) Component dipentaerythritol hexaacrylate DPHA (manufactured by Nippon Kayaku Co., Ltd.) 4.8 g was added and stirred. Next, 351.5 g of Green dispersion C composed of component (D), a dispersant, and a solvent, which were previously dispersed and prepared, was added and further stirred. Finally, 3.0 g and 0.3 g of the additive silane coupling agent and surfactant were added, and the mixture was further stirred for 30 minutes to obtain a test ink composition. The composition and evaluation results are shown in Table 2.
［比較例１］
ビーカー（1000ml）に回転子を入れ、マグネチックスターラーに設置した。溶剤としてBCAを118.5g秤量し、攪拌しながら（Ｃ）成分としてYX4000HK (ジャパンエポキシレジン社製)を1.2g加えた。これらの溶解を確認した後、（Ａ）成分のフルオレン型エポキシ型アクリレート／酸無水物重合付加体のPGMEA溶液（新日鐵化学(株)製 Ｖ259ME 樹脂成分等56.5％）を12.2gと（B）成分のジペンタエリスリトールヘキサアクリレートDPHA（日本化薬社製）4.6ｇとを添加して、攪拌した。次に、あらかじめ分散、調製した（Ｄ）成分、分散剤及び溶剤からなるGreen分散体Ｄを363.5g加えて更に攪拌した。最後に添加剤のシランカップリング剤と界面活性剤を各2.5gと0.3g添加した後、さらに30分攪拌して試験用インキ組成物を得た。組成及び評価結果を表２に示す。
[Comparative Example 1]
The rotor was placed in a beaker (1000 ml) and placed on a magnetic stirrer. 118.5 g of BCA was weighed as a solvent, and 1.2 g of YX4000HK (manufactured by Japan Epoxy Resin Co., Ltd.) was added as component (C) while stirring. After confirming their dissolution, 12.2 g of PGMEA solution of component (A), fluorene type epoxy acrylate / acid anhydride polymerization adduct (V259ME resin component 56.5%, manufactured by Nippon Steel Chemical Co., Ltd.) ) Component dipentaerythritol hexaacrylate DPHA (manufactured by Nippon Kayaku Co., Ltd.) (4.6 g) was added and stirred. Next, 363.5 g of Green dispersion D composed of component (D), a dispersant and a solvent, which had been dispersed and prepared in advance, was added and further stirred. Finally, 2.5 g and 0.3 g of the additive silane coupling agent and surfactant were added, and the mixture was further stirred for 30 minutes to obtain a test ink composition. The composition and evaluation results are shown in Table 2.
［比較例２］
ビーカー（1000ml）に回転子を入れ、マグネチックスターラーに設置した。溶剤としてBCAを96.5g秤量し、攪拌しながら（Ｃ）成分としてYX4000HK (ジャパンエポキシレジン社製)を3.5g加えた。これらの溶解を確認した後、（Ａ）成分のフルオレン型エポキシ型アクリレート／酸無水物重合付加体のPGMEA溶液（新日鐵化学(株)製 Ｖ259ME 樹脂成分等56.5％）を35.0gと（Ｂ）成分のジペンタエリスリトールヘキサアクリレートDPHA（日本化薬社製）13.5ｇとを添加して、攪拌した。次に、あらかじめ分散、調製した（Ｄ）成分、分散剤及び溶剤からなるGreen分散液Aを351.5g加えて更に攪拌した。最後に添加剤のシランカップリング剤と界面活性剤を各2.5gと0.3g添加した後、さらに30分攪拌して試験用インキ組成物を得た。組成及び評価結果を表２に示す。
[Comparative Example 2]
The rotor was placed in a beaker (1000 ml) and placed on a magnetic stirrer. 96.5 g of BCA was weighed as a solvent, and 3.5 g of YX4000HK (manufactured by Japan Epoxy Resin Co., Ltd.) was added as component (C) while stirring. After confirming these dissolutions, 35.0 g of PGMEA solution (5259% V259ME resin component, etc., manufactured by Nippon Steel Chemical Co., Ltd.) of (A) component fluorene type epoxy acrylate / anhydride polymer adduct 13.5 g of dipentaerythritol hexaacrylate DPHA (manufactured by Nippon Kayaku Co., Ltd.) was added and stirred. Next, 351.5 g of Green dispersion A composed of component (D), a dispersant and a solvent, which had been dispersed and prepared in advance, was added and further stirred. Finally, 2.5 g and 0.3 g of the additive silane coupling agent and surfactant were added, and the mixture was further stirred for 30 minutes to obtain a test ink composition. The composition and evaluation results are shown in Table 2.
［比較例３］
ビーカー（1000ml）に回転子を入れ、マグネチックスターラーに設置した。溶剤としてBCAを206.2g秤量し、攪拌しながら（Ｃ）成分としてYX4000HK (ジャパンエポキシレジン社製)を3.1g加えた。これらの溶解を確認した後、（Ａ）成分のフルオレン型エポキシ型アクリレート／酸無水物重合付加体のPGMEA溶液（新日鐵化学(株)製 Ｖ259ME 樹脂成分等56.5％）を32.2gと（Ｂ）成分のジペンタエリスリトールヘキサアクリレートDPHA（日本化薬社製）12.4ｇとを添加して、攪拌した。次に、あらかじめ分散、調製した（Ｄ）成分、分散剤及び溶剤からなるRed分散体Ａを246.1g加えて更に攪拌した。最後に添加剤のシランカップリング剤と界面活性剤を各2.5gと0.3g添加した後、さらに30分攪拌して試験用インキ組成物を得た。組成及び評価結果を表２に示す。
[Comparative Example 3]
The rotor was placed in a beaker (1000 ml) and placed on a magnetic stirrer. 206.2 g of BCA was weighed as a solvent, and 3.1 g of YX4000HK (manufactured by Japan Epoxy Resin Co., Ltd.) was added as component (C) while stirring. After confirming the dissolution, 32.2 g of PGMEA solution (5259% V259ME resin component, etc., manufactured by Nippon Steel Chemical Co., Ltd.) of (A) component fluorene type epoxy acrylate / acid anhydride polymerization adduct was obtained (B ) Component dipentaerythritol hexaacrylate DPHA (manufactured by Nippon Kayaku Co., Ltd.) 12.4 g was added and stirred. Next, 246.1 g of Red dispersion A composed of component (D), a dispersant and a solvent previously dispersed and added was added and further stirred. Finally, 2.5 g and 0.3 g of the additive silane coupling agent and surfactant were added, and the mixture was further stirred for 30 minutes to obtain a test ink composition. The composition and evaluation results are shown in Table 2.
［比較例４］
ビーカー（1000ml）に回転子を入れ、マグネチックスターラーに設置した。溶剤としてBCAを146.0g秤量し、攪拌しながら（Ａ）成分のフルオレン型エポキシ型アクリレート／酸無水物重合付加体のPGMEA溶液（新日鐵化学(株)製 Ｖ259ME 樹脂成分等56.5％）を48.5gと（Ｂ）成分のジペンタエリスリトールヘキサアクリレートDPHA（日本化薬社製）18.5ｇとを添加して、攪拌した。次に、あらかじめ分散、調製した（Ｄ）成分、分散剤及び溶剤からなるBlue分散体Ａを287.0g加えて更に攪拌した。最後に添加剤のシランカップリング剤と界面活性剤を各2.5gと0.3g添加した後、さらに30分攪拌して試験用インキ組成物を得た。組成及び評価結果を表２に示す。
[Comparative Example 4]
The rotor was placed in a beaker (1000 ml) and placed on a magnetic stirrer. Weigh 146.0 g of BCA as a solvent, and stir 48.5 g of PGMEA solution of component (A) fluorene type epoxy acrylate / acid anhydride polymerization adduct (V259ME resin component 56.5% made by Nippon Steel Chemical Co., Ltd.) g and 18.5 g of component (B) dipentaerythritol hexaacrylate DPHA (manufactured by Nippon Kayaku Co., Ltd.) were added and stirred. Next, 287.0 g of Blue dispersion A composed of component (D), a dispersing agent and a solvent previously dispersed and prepared was added and further stirred. Finally, 2.5 g and 0.3 g of the additive silane coupling agent and surfactant were added, and the mixture was further stirred for 30 minutes to obtain a test ink composition. The composition and evaluation results are shown in Table 2.
上記で得られた試験用インキ組成物を下記手順により評価し、結果を表２に示した。 The test ink composition obtained above was evaluated by the following procedure, and the results are shown in Table 2.
<粘度安定性試験>
作製したインキ組成物は、先にE型粘度計にて50rpm、23℃の粘度を測定した。その後、100ｇを密封できる容器に移し、40℃で一週間加速エージング後、同様の条件にて粘度を測定し、初期粘度より粘度上昇が１ｍPa・sec以下を合格とした。
<Viscosity stability test>
The prepared ink composition was previously measured for its viscosity at 50 rpm and 23 ° C. with an E-type viscometer. Thereafter, 100 g was transferred to a container that could be sealed, and after accelerated aging at 40 ° C. for one week, the viscosity was measured under the same conditions, and a viscosity increase of 1 mPa · sec or less from the initial viscosity was accepted.
〈吐出試験〉
東芝テック社製ヘッド（CA-3）に接続し、パージ、洗浄を実施後、インキ組成物の吐出状態をストロボカメラにて確認し、液滴が吐出しない、飛翔軌道が明らかに垂直でないなど著しい不具合がなければ○とした。この試験での合格レベルの様子を図１に示す。
<Discharge test>
Connected to Toshiba Tec head (CA-3), purged and washed, checked ink composition ejection status with strobe camera, no droplets ejected, flight trajectory not clearly vertical, etc. If there was no defect, it was rated as “Good”. The state of the pass level in this test is shown in FIG.
<NMP 浸漬試験>
インキ組成物を塗布、硬化したガラス基板を5cm角に切断し、室温にて24時間、NMP (N-メチルピロリドン)に浸漬後、塗膜の変色（ΔE＜３で合格）と膜の剥離やクラックの発生の有無を確認した。
<NMP immersion test>
A glass substrate coated and cured with an ink composition is cut into 5 cm squares, immersed in NMP (N-methylpyrrolidone) for 24 hours at room temperature, then discolored (passed with ΔE <3) and film peeling The presence or absence of cracks was confirmed.
<耐熱試験>
インキ組成物を塗布、硬化したガラス基板を5cm角に切断し250℃に設定したオーブン内に1時間置いた後、塗膜の変色（ΔE＜３で合格）と膜の剥離やクラックの発生の有無を確認した。
<Heat resistance test>
A glass substrate coated and cured with an ink composition is cut into 5 cm squares and placed in an oven set at 250 ° C. for 1 hour, and then the coating color changes (passes ΔE <3) and film peeling or cracking occurs. The presence or absence was confirmed.
<液晶汚染性試験（VHR）>
インキ組成物を塗布、硬化したガラス基板から硬化膜を20ｍｇ採取し、ドラフト内で液晶ZLI4792 1.0ｇを秤量したスクリュー管に混合し、密閉する。これを100℃/72hの条件でエージングさせた後、測定用ガラスセルに液晶を注入した。このセルを東陽テクニカ製 電圧保持率測定システム（VHR-1A）にセットし測定した。その結果、保持率が９５％以上を合格とした。
<Liquid crystal contamination test (VHR)>
20 mg of a cured film is collected from a glass substrate coated and cured with the ink composition, mixed in a screw tube in which 1.0 g of liquid crystal ZLI4792 is weighed in a draft, and sealed. After this was aged at 100 ° C./72 h, liquid crystal was injected into the glass cell for measurement. This cell was set in a voltage holding ratio measurement system (VHR-1A) manufactured by Toyo Technica and measured. As a result, a retention rate of 95% or more was considered acceptable.
<総合評価>
上記評価試験の結果を一覧し、すべてが合格となった場合に合格判定とした。
<Comprehensive evaluation>
The results of the above evaluation tests were listed, and when all passed, it was determined as acceptable.
Claims (8)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013121750A JP2013238859A (en) | 2013-06-10 | 2013-06-10 | Ink composition for inkjet color filter superior in storage stability, and cured film of inkjet color filter and color filter obtained by using ink composition |
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| JP2013121750A JP2013238859A (en) | 2013-06-10 | 2013-06-10 | Ink composition for inkjet color filter superior in storage stability, and cured film of inkjet color filter and color filter obtained by using ink composition |
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| JP2008191325A Division JP5324850B2 (en) | 2008-07-24 | 2008-07-24 | Ink composition for ink jet color filter excellent in storage stability, ink-jet color filter cured film and color filter obtained using this ink composition |
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Citations (9)
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|---|---|---|---|---|
| JP2001240780A (en) * | 2000-02-29 | 2001-09-04 | Nippon Steel Chem Co Ltd | Red color resist ink and color filter |
| JP2003066223A (en) * | 2001-06-15 | 2003-03-05 | Nof Corp | Ink jet ink composition for color filter, method for manufacturing ink composition and method for manufacturing color filter |
| JP2006003860A (en) * | 2003-11-26 | 2006-01-05 | Nippon Steel Chem Co Ltd | Photosensitive resin composition and color filter using the same |
| JP2006002128A (en) * | 2004-05-19 | 2006-01-05 | Mitsubishi Chemicals Corp | Curable resin composition for inkjet, color filter and liquid crystal display device |
| JP2007133120A (en) * | 2005-11-10 | 2007-05-31 | Nippon Steel Chem Co Ltd | Ink composition for color filter, and cured film of color filter and color filter obtained using the ink composition |
| JP2007256700A (en) * | 2006-03-24 | 2007-10-04 | Nippon Steel Chem Co Ltd | Composition for color filter and color filter |
| JP2007264433A (en) * | 2006-03-29 | 2007-10-11 | Nippon Steel Chem Co Ltd | Photosensitive resin composition and color filter |
| JP2008009401A (en) * | 2006-06-01 | 2008-01-17 | Nippon Steel Chem Co Ltd | Resist composition for color filter, method for producing the same, and color filter using the same |
| JP2008191325A (en) * | 2007-02-02 | 2008-08-21 | Toshiba Matsushita Display Technology Co Ltd | Display device |
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- 2013-06-10 JP JP2013121750A patent/JP2013238859A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001240780A (en) * | 2000-02-29 | 2001-09-04 | Nippon Steel Chem Co Ltd | Red color resist ink and color filter |
| JP2003066223A (en) * | 2001-06-15 | 2003-03-05 | Nof Corp | Ink jet ink composition for color filter, method for manufacturing ink composition and method for manufacturing color filter |
| JP2006003860A (en) * | 2003-11-26 | 2006-01-05 | Nippon Steel Chem Co Ltd | Photosensitive resin composition and color filter using the same |
| JP2006002128A (en) * | 2004-05-19 | 2006-01-05 | Mitsubishi Chemicals Corp | Curable resin composition for inkjet, color filter and liquid crystal display device |
| JP2007133120A (en) * | 2005-11-10 | 2007-05-31 | Nippon Steel Chem Co Ltd | Ink composition for color filter, and cured film of color filter and color filter obtained using the ink composition |
| JP2007256700A (en) * | 2006-03-24 | 2007-10-04 | Nippon Steel Chem Co Ltd | Composition for color filter and color filter |
| JP2007264433A (en) * | 2006-03-29 | 2007-10-11 | Nippon Steel Chem Co Ltd | Photosensitive resin composition and color filter |
| JP2008009401A (en) * | 2006-06-01 | 2008-01-17 | Nippon Steel Chem Co Ltd | Resist composition for color filter, method for producing the same, and color filter using the same |
| JP2008191325A (en) * | 2007-02-02 | 2008-08-21 | Toshiba Matsushita Display Technology Co Ltd | Display device |
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