JP2011048004A - Photosensitive red composition for color filter, and color filter using the same - Google Patents
Photosensitive red composition for color filter, and color filter using the same Download PDFInfo
- Publication number
- JP2011048004A JP2011048004A JP2009194281A JP2009194281A JP2011048004A JP 2011048004 A JP2011048004 A JP 2011048004A JP 2009194281 A JP2009194281 A JP 2009194281A JP 2009194281 A JP2009194281 A JP 2009194281A JP 2011048004 A JP2011048004 A JP 2011048004A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- color filter
- red composition
- photosensitive red
- photosensitive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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Abstract
Description
本発明は、カラーフィルターに有用な感光性赤色組成物及びそれを用いたカラーフィルターに関する。 The present invention relates to a photosensitive red composition useful for a color filter and a color filter using the same.
一般に液晶表示装置等に用いられるカラーフィルターを製造する方法としては、顔料分散法、染色法、電着法、印刷法、インクジェット法が知られている。そのなかでも顔料分散法が最も広範に採用されている。
ところで、近年、カラーフィルターに対しては、更なる高透過率、かつ高コントラストが要求されてきた。例えば、特許文献１では、高透過率を得るべく、顔料分散法によるＣ．Ｉ．ピグメントオレンジ３８（以下、「ＰＯ３８」という）及びＣ．Ｉ．ピグメントレッド２５４（以下、「ＰＲ２５４」という）を含有するカラーフィルター用赤色組成物が提案されている。
また、特許文献２では、顔料分散法によるＰＯ３８を２０重量％以上含むカラーフィルターの赤色画素形成用感放射線性組成物が提案されている。
しかしながら、これらの場合、ＰＯ３８の分散が困難であるという問題があった。
As a method for producing a color filter generally used for a liquid crystal display device or the like, a pigment dispersion method, a dyeing method, an electrodeposition method, a printing method, and an ink jet method are known. Among them, the pigment dispersion method is most widely adopted.
Incidentally, in recent years, color filters have been required to have higher transmittance and higher contrast. For example, in Patent Document 1, in order to obtain high transmittance, C.I. I. Pigment Orange 38 (hereinafter referred to as “PO38”) and C.I. I. A red composition for a color filter containing Pigment Red 254 (hereinafter referred to as “PR254”) has been proposed.
Further, Patent Document 2 proposes a radiation sensitive composition for forming a red pixel of a color filter containing 20% by weight or more of PO38 by a pigment dispersion method.
However, in these cases, there is a problem that dispersion of PO38 is difficult.
本発明は、このような状況下で、ＰＯ３８を微細に、かつ安定に分散し、粘度変化の少ない、高透過率で高コントラストの感光性赤色組成物及びそれを用いたカラーフィルターを提供することを課題とするものである。 Under such circumstances, the present invention provides a photosensitive red composition having a high transmittance and a high contrast, in which PO38 is finely and stably dispersed, has a small viscosity change, and a color filter using the same. Is an issue.
本発明者は、前記課題を達成するために鋭意研究を重ねた結果、ＰＯ３８とＰＲ２５４とを適切な質量比で用いると共に、特定の顔料誘導体、バインダー樹脂及び分散剤を用いることにより上記課題を達成し得ることを見出した。本発明は、かかる知見に基づいて完成したものである。
すなわち、本発明は、
［１］少なくとも（Ａ）顔料、（Ｂ）顔料誘導体、（Ｃ）分散剤、（Ｄ）バインダー樹脂、（Ｅ）光重合性モノマー、（Ｆ）光重合開始剤及び（Ｇ）溶剤を含有する感光性赤色組成物であって、（Ａ）顔料がＰＯ３８とＰＲ２５４を含有し、顔料中の（ＰＯ３８／ＰＲ２５４）の質量比が（５１／４９）〜（８０／２０）であり、（Ｂ）顔料誘導体がＰＯ３８から得られるスルホン酸基を有する化合物を含有し、（Ｃ）分散剤のアミン価が１〜２００ｍｇＫＯＨ／ｇであり、かつ（Ｄ）バインダー樹脂が側鎖に少なくとも水酸基及びエチレン性不飽和二重結合基を有する樹脂を含有することを特徴とするカラーフィルター用感光性赤色組成物、
［２］上記［１］に記載のカラーフィルター用感光性赤色組成物を有するカラーフィルター、及び
［３］Ｃ光源及び２°視野の条件において、ＸＹＺ表色系色度図における色度座標（ｘ，ｙ）が以下の範囲にある上記［２］に記載のカラーフィルターである。
０．５４０≦ｘ≦０．６７０
０．３３６≦ｙ≦０．３４９
As a result of intensive studies to achieve the above-mentioned problems, the present inventor achieved the above-mentioned problems by using PO38 and PR254 at an appropriate mass ratio and using specific pigment derivatives, binder resins and dispersants. I found out that I could do it. The present invention has been completed based on such findings.
That is, the present invention
[1] Contains at least (A) pigment, (B) pigment derivative, (C) dispersant, (D) binder resin, (E) photopolymerizable monomer, (F) photopolymerization initiator, and (G) solvent. A photosensitive red composition, wherein (A) the pigment contains PO38 and PR254, and the mass ratio of (PO38 / PR254) in the pigment is (51/49) to (80/20), (B) The pigment derivative contains a compound having a sulfonic acid group obtained from PO38, (C) the dispersant has an amine value of 1 to 200 mgKOH / g, and (D) the binder resin has at least hydroxyl groups and ethylenic groups in the side chain. A photosensitive red composition for color filters, comprising a resin having a saturated double bond group;
[2] A chromaticity coordinate (x) in an XYZ color system chromaticity diagram under the conditions of a color filter having the photosensitive red composition for a color filter described in [1] above, and [3] a C light source and a 2 ° visual field. , Y) is the color filter according to the above [2], which is in the following range.
0.540 ≦ x ≦ 0.670
0.336 ≦ y ≦ 0.349
本発明によれば、ＰＯ３８を微細に、かつ安定に分散し、粘度変化の少ない、高透過率で高コントラストの感光性赤色組成物及びそれを用いたカラーフィルターを提供することができる。 According to the present invention, it is possible to provide a photosensitive red composition having a high transmittance and a high contrast, in which PO38 is finely and stably dispersed, having a small viscosity change, and a color filter using the same.
本発明のカラーフィルター用感光性赤色組成物は、少なくとも（Ａ）顔料、（Ｂ）顔料誘導体、（Ｃ）分散剤、（Ｄ）バインダー樹脂、（Ｅ）光重合性モノマー、（Ｆ）光重合開始剤及び（Ｇ）溶剤を含有する感光性赤色組成物であって、（Ａ）顔料がＰＯ３８とＰＲ２５４を含有し、顔料中の（ＰＯ３８／ＰＲ２５４）の質量比が（５１／４９）〜（８０／２０）であり、（Ｂ）顔料誘導体がＰＯ３８から得られるスルホン酸基を有する化合物を含有し、（Ｃ）分散剤のアミン価が１〜２００ｍｇＫＯＨ／ｇであり、かつ（Ｄ）バインダー樹脂が側鎖に少なくとも水酸基及びエチレン性不飽和二重結合基を有する樹脂を含有することを特徴とする。
ここで、ＰＯ３８はナフトール構造を有するオレンジ顔料であり、ＰＲ２５４は、ＤＰＰ（ジケトピロロピロール）構造を有するレッド顔料である。
The photosensitive red composition for color filter of the present invention comprises at least (A) a pigment, (B) a pigment derivative, (C) a dispersant, (D) a binder resin, (E) a photopolymerizable monomer, and (F) a photopolymerization. A photosensitive red composition containing an initiator and (G) a solvent, wherein (A) the pigment contains PO38 and PR254, and the mass ratio of (PO38 / PR254) in the pigment is (51/49) to ( 80/20), (B) the pigment derivative contains a compound having a sulfonic acid group obtained from PO38, (C) the amine value of the dispersant is 1 to 200 mgKOH / g, and (D) the binder resin. Contains a resin having at least a hydroxyl group and an ethylenically unsaturated double bond group in the side chain.
Here, PO38 is an orange pigment having a naphthol structure, and PR254 is a red pigment having a DPP (diketopyrrolopyrrole) structure.
本発明のカラーフィルター用感光性赤色組成物は、上記の（Ａ）顔料と、（Ｂ）顔料誘導体と、（Ｃ）分散剤と、（Ｄ）バインダー樹脂と、（Ｅ）光重合性モノマーと、（Ｆ）光重合性開始剤と、（Ｇ）溶剤と、所望により添加される添加剤とを混合分散して得られる。（Ａ）顔料と上記成分の一部を混合分散して、顔料分散液を作成し、さらに、残りの成分を添加、混合分散して本発明の感光性赤色組成物を作成しても良い。
混合分散はペイントシェイカー、ビーズミル、ボールミル、ディゾルバー、ニーダー、ロールミル、高圧分散機、ホモミキサ等の混合分散機を使用して行われる。
上記（Ａ）顔料を分散する際には、側鎖に水酸基及びエチレン性不飽和二重結合基を有するバインダー樹脂を添加することが好ましく、アミン価が１〜２００ｍｇＫＯＨ／ｇの分散剤を添加することが好ましい。顔料分散液の分散性が向上するからである。
また、ＰＯ３８から得られるスルホン酸基を有する顔料誘導体は顔料を作成する際に添加しても良いし、顔料分散液を混合分散する際に添加しても良いし、感光性赤色組成物を混合分散する際に添加しても良い。
The photosensitive red composition for a color filter of the present invention comprises the above (A) pigment, (B) a pigment derivative, (C) a dispersant, (D) a binder resin, and (E) a photopolymerizable monomer. , (F) a photopolymerizable initiator, (G) a solvent, and an additive that is optionally added are mixed and dispersed. (A) The pigment and a part of the above components may be mixed and dispersed to prepare a pigment dispersion, and the remaining components may be added and mixed and dispersed to prepare the photosensitive red composition of the present invention.
Mixing / dispersing is performed using a mixing / dispersing machine such as a paint shaker, a bead mill, a ball mill, a dissolver, a kneader, a roll mill, a high-pressure disperser, or a homomixer.
When dispersing the pigment (A), it is preferable to add a binder resin having a hydroxyl group and an ethylenically unsaturated double bond group in the side chain, and a dispersant having an amine value of 1 to 200 mgKOH / g is added. It is preferable. This is because the dispersibility of the pigment dispersion is improved.
Further, the pigment derivative having a sulfonic acid group obtained from PO38 may be added when preparing the pigment, or may be added when mixing and dispersing the pigment dispersion, or mixing the photosensitive red composition. It may be added when dispersing.
本発明のカラーフィルター用感光性赤色組成物は、顔料中の（ＰＯ３８／ＰＲ２５４）の質量比が（５１／４９）〜（８０／２０）の範囲内であることを要する。質量比が（５１／４９）より小さいと高透過率を達成できなくなり、また、質量比が（８０／２０）より大きいと、表示色が赤色ではなくオレンジ色となり、所望の分光特性から外れるからである。これらの観点から、上記質量比が（６２／３８）〜（７５／２５）であることが好ましい。
さらに、顔料中のＰＯ３８とＰＲ２５４の合計量は、９０〜１００質量％であることが好ましい。上記範囲内であれば、高透過率を達成できるからである。
また、本発明の感光性赤色組成物の固形成分中の顔料の量は、好ましくは５〜５０質量％、特に好ましくは１０〜４５質量％である。５質量％以上であれば、本発明の感光性赤色組成物を用いてカラーフィルターを形成した場合に現像残渣が発生することを好適に防ぐことができると共に、現像性を好適に確保できるからである。また、５０質量％以下であれば、本発明の感光性赤色組成物を用いてカラーフィルターを形成した場合に、着色層の発色が好適に十分なものとなるからである。
The photosensitive red composition for color filter of the present invention requires that the mass ratio of (PO38 / PR254) in the pigment is in the range of (51/49) to (80/20). If the mass ratio is smaller than (51/49), high transmittance cannot be achieved, and if the mass ratio is larger than (80/20), the display color becomes orange instead of red, which is out of the desired spectral characteristics. It is. From these viewpoints, the mass ratio is preferably (62/38) to (75/25).
Furthermore, the total amount of PO38 and PR254 in the pigment is preferably 90 to 100% by mass. This is because high transmittance can be achieved within the above range.
Moreover, the amount of the pigment in the solid component of the photosensitive red composition of the present invention is preferably 5 to 50% by mass, particularly preferably 10 to 45% by mass. If it is 5% by mass or more, it is possible to suitably prevent development residue when the color filter is formed using the photosensitive red composition of the present invention, and it is possible to suitably ensure developability. is there. Moreover, if it is 50 mass% or less, when a color filter is formed using the photosensitive red composition of the present invention, the color of the colored layer is suitably sufficient.
本発明のカラーフィルター用感光性赤色組成物は、ＰＯ３８から得られるスルホン酸基を有する化合物を含有する顔料誘導体を含むことを要する。本発明のカラーフィルター用感光性赤色組成物の分散性の向上のためである。このＰＯ３８から得られるスルホン酸基を有する化合物は、例えば、次のような方法により合成される。ＰＯ３８を濃硫酸、発煙硫酸、クロロスルホン酸、又はこれらの混合液などに投入してスルホン化反応を行う。得られた反応液を水で希釈し、場合により金属アルカリ水溶液あるいはアミン又はその水溶液で中和する。このようにして得られた懸濁液をろ過した後に水系の洗浄液で洗浄し、乾燥する。 The photosensitive red composition for a color filter of the present invention needs to contain a pigment derivative containing a compound having a sulfonic acid group obtained from PO38. This is for improving the dispersibility of the photosensitive red composition for a color filter of the present invention. The compound having a sulfonic acid group obtained from PO38 is synthesized, for example, by the following method. PO38 is added to concentrated sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, or a mixture thereof to carry out the sulfonation reaction. The resulting reaction solution is diluted with water and optionally neutralized with a metal alkali aqueous solution or an amine or an aqueous solution thereof. The suspension thus obtained is filtered, washed with an aqueous washing solution, and dried.
上記の合成過程で中和を行う場合、金属アルカリ水溶液もしくはアミン水溶液を用いるが、好ましくはアミン水溶液を用いるほうが良い。中和に用いるアミン水溶液としてはアンモニア、モノエタノールアミン、トリエタノールアミン、テトラメチルアンモニウムヒドロキシドなどの水溶液を用いることができる。本発明では特にこれらに限定されずに種々のアミン水溶液を使用することができるが、アンモニアの使用がその揮発のしやすさから好ましい。 When neutralization is performed in the above synthesis process, a metal alkali aqueous solution or an amine aqueous solution is used, but an amine aqueous solution is preferably used. As the aqueous amine solution used for neutralization, aqueous solutions of ammonia, monoethanolamine, triethanolamine, tetramethylammonium hydroxide and the like can be used. In the present invention, various amine aqueous solutions can be used without being limited to these, but the use of ammonia is preferred because of its ease of volatilization.
本発明において用いられる、ＰＯ３８から得られるスルホン酸基を有する化合物を含有する顔料誘導体の、１分子あたりのスルホン酸基の平均導入数は、好ましくは１個〜４個、より好ましくは１．１個〜３個である。スルホン酸基の導入数が少なすぎると、顔料粒子間の静電反発力が弱くなり分散不安定化する場合がある。スルホン酸基の導入数が多すぎると、極性が高過ぎて分散不安定化する場合がある。
また、ＰＯ３８から得られるスルホン酸基を有する化合物を含有する顔料誘導体は、本発明のカラーフィルター用感光性赤色組成物に含まれるＰＯ３８の質量１００質量部に対して１〜１５質量部、好ましくは２〜１０質量部含まれることが好ましい。１質量部以上であれば感光性赤色組成物の分散安定性がより向上し、１５質量部以下であれば感光性赤色組成物の色調ずれや輝度低下を好適に防止することができる。
The average number of sulfonic acid groups introduced per molecule of the pigment derivative containing a compound having a sulfonic acid group obtained from PO38 used in the present invention is preferably 1 to 4, more preferably 1.1. 3 to 3. If the number of introduced sulfonic acid groups is too small, the electrostatic repulsion between the pigment particles may be weakened and the dispersion may become unstable. If the number of sulfonic acid groups introduced is too large, the polarity may be too high and the dispersion may become unstable.
Further, the pigment derivative containing a compound having a sulfonic acid group obtained from PO38 is 1 to 15 parts by mass, preferably 100 parts by mass of PO38 contained in the photosensitive red composition for color filter of the present invention, preferably It is preferable that 2-10 mass parts is contained. When the amount is 1 part by mass or more, the dispersion stability of the photosensitive red composition is further improved, and when the amount is 15 parts by mass or less, a color shift or a decrease in luminance of the photosensitive red composition can be suitably prevented.
本発明のカラーフィルター用感光性赤色組成物は、さらに、アミン価１〜２００ｍｇＫＯＨ／ｇの分散剤を含有することを要する。本発明のカラーフィルター用感光性赤色組成物の分散性の向上のためである。アミン価が１〜２００ｍｇＫＯＨ／ｇの分散剤としては、高分子分散剤が好ましく、各種市販されている。例えば、Disperbyk-161（アミン価：３６．６ｍｇＫＯＨ／ｇ、ビックケミー社製）、Disperbyk-162（アミン価：３４．２ｍｇＫＯＨ／ｇ、ビックケミー社製）、Disperbyk-163（アミン価：２２．２ｍｇＫＯＨ／ｇ、ビックケミー社製）、Disperbyk-164（アミン価：３０ｍｇＫＯＨ／ｇ、ビックケミー社製）、Disperbyk-166（アミン価：６６．７ｍｇＫＯＨ／ｇ、ビックケミー社製）、Disperbyk-167（アミン価：２５ｍｇＫＯＨ／ｇ、ビックケミー社製）、Disperbyk-182（アミン価：２５ｍｇＫＯＨ／ｇ、ビックケミー社製）、Disperbyk-2000（アミン価：１０ｍｇＫＯＨ／ｇ、ビックケミー社製）、Disperbyk-2001（アミン価：６３ｍｇＫＯＨ／ｇ、ビックケミー社製）、BYK LPN-6919（アミン価：１８０ｍｇＫＯＨ／ｇ、ビックケミー社製）、BYK LPN-21116（アミン価：７２．５ｍｇＫＯＨ／ｇ、ビックケミー社製）等が挙げられる。
なお、アミン価は、ＡＳＴＭ Ｄ ２０７４に準拠して測定される。
本発明のカラーフィルター用感光性赤色組成物に用いられる（Ｃ）分散剤の使用量は、（Ａ）顔料１００質量部に対して、１０〜６０質量部であることが好ましい。１０質量部以上であれば顔料の分散性を好適に確保でき、６０質量部以下であれば現像性を良好にできるからである。
The photosensitive red composition for a color filter of the present invention further needs to contain a dispersant having an amine value of 1 to 200 mgKOH / g. This is for improving the dispersibility of the photosensitive red composition for a color filter of the present invention. As the dispersant having an amine value of 1 to 200 mgKOH / g, a polymer dispersant is preferable, and various types are commercially available. For example, Disperbyk-161 (amine value: 36.6 mgKOH / g, manufactured by Big Chemie), Disperbyk-162 (amine value: 34.2 mgKOH / g, manufactured by Big Chemie), Disperbyk-163 (amine value: 22.2 mgKOH / g) , Manufactured by Big Chemie), Disperbyk-164 (amine value: 30 mg KOH / g, manufactured by Big Chemie), Disperbyk-166 (amine value: 66.7 mg KOH / g, manufactured by Big Chemie), Disperbyk-167 (amine value: 25 mg KOH / g) , Manufactured by Big Chemie), Disperbyk-182 (amine value: 25 mg KOH / g, manufactured by Big Chemie), Disperbyk-2000 (amine value: 10 mg KOH / g, manufactured by Big Chemie), Disperbyk-2001 (amine value: 63 mg KOH / g, Big Chemie) BYK LPN-6919 (amine value: 180 mg KOH / g, manufactured by BYK Chemie), BYK LPN-21116 (amine value: 72.5 mg) OH / g, and the like is manufactured by BYK-Chemie GmbH), and the like.
The amine value is measured according to ASTM D 2074.
It is preferable that the usage-amount of the (C) dispersing agent used for the photosensitive red composition for color filters of this invention is 10-60 mass parts with respect to 100 mass parts of (A) pigment. This is because the dispersibility of the pigment can be suitably ensured if it is 10 parts by mass or more, and the developability can be improved if it is 60 parts by mass or less.
また、本発明においては、（Ｄ）バインダー樹脂が側鎖に水酸基及びエチレン性不飽和二重結合基を有する樹脂を含有することを要する。水酸基と顔料誘導体中のスルホン基との相互作用により、分散液及び／又は感光性赤色組成物の分散経時安定性が増し、またエチレン性不飽和二重結合により感光性赤色組成物の硬化性が向上するからである。
具体的には、カルボキシル基等の酸性官能基を有するアルカリ可溶性樹脂に、分子内にエポキシ基とエチレン性不飽和基とを併せ持つ化合物、例えばグリシジル（メタ）アクリレート、グリシジルα−エチルアクリレート、（３，４−エポキシシクロヘキシル）メチル（メタ）アクリレート、クロトニルグリシジルエーテル、クロトン酸グリシジルエーテル、イソクロトン酸グリシジルエーテル等を付加させ、側鎖に水酸基とエチレン性不飽和基を導入したものを挙げることができる。カルボキシル基を有するアルカリ可溶性樹脂としては、カルボキシル基含有不飽和単量体と他の共重合可能なエチレン性不飽和単量体の共重合体が好ましい。
Moreover, in this invention, it is required for (D) binder resin to contain resin which has a hydroxyl group and an ethylenically unsaturated double bond group in a side chain. Due to the interaction between the hydroxyl group and the sulfone group in the pigment derivative, the dispersion aging stability of the dispersion and / or the photosensitive red composition is increased, and the curability of the photosensitive red composition is increased by the ethylenically unsaturated double bond. It is because it improves.
Specifically, an alkali-soluble resin having an acidic functional group such as a carboxyl group and a compound having both an epoxy group and an ethylenically unsaturated group in the molecule, such as glycidyl (meth) acrylate, glycidyl α-ethyl acrylate, (3 , 4-epoxycyclohexyl) methyl (meth) acrylate, crotonyl glycidyl ether, crotonic acid glycidyl ether, isocrotonic acid glycidyl ether, and the like, and a hydroxyl group and an ethylenically unsaturated group are introduced into the side chain. . The alkali-soluble resin having a carboxyl group is preferably a copolymer of a carboxyl group-containing unsaturated monomer and another copolymerizable ethylenically unsaturated monomer.
カルボキシル基含有不飽和単量体としては、例えば、（メタ）アクリル酸、クロトン酸、マレイン酸、無水マレイン酸、コハク酸モノ［２−（メタ）アクリロイロキシエチル］、フタル酸モノ［２−（メタ）アクリロイロキシエチル］、ω−カルボキシポリカプロラクトンモノ（メタ）アクリレート等が好ましく、（メタ）アクリル酸が特に好ましい。なお、カルボキシル基含有不飽和単量体は、単独もしくは数種類を組み合わせることができる。 Examples of the carboxyl group-containing unsaturated monomer include (meth) acrylic acid, crotonic acid, maleic acid, maleic anhydride, succinic acid mono [2- (meth) acryloyloxyethyl], and phthalic acid mono [2- (Meth) acryloyloxyethyl], ω-carboxypolycaprolactone mono (meth) acrylate and the like are preferable, and (meth) acrylic acid is particularly preferable. In addition, the carboxyl group-containing unsaturated monomer can be used alone or in combination of several kinds.
エチレン性不飽和単量体としては、メチル（メタ）アクリレート、ｎ−ブチル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、イソボルニル（メタ）アクリレート、ジシクロペンタニル（メタ）アクリレート、ジシクロペンテニル（メタ）アクリレート、アリル（メタ）アクリレート、スチレン、α−メチルスチレン、ベンジル（メタ）アクリレート、ヒドロキシエチル（メタ）アクリレート、２−ジメチルアミノエチル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、２−ヒドロキシル（メタ）エチルアクリレート等、及び、これらのマクロモノマー類；Ｎ−メチルマレイミド、Ｎ−シクロヘキシルマレイミド、Ｎ−ベンジルマレイミド、Ｎ−フェニルマレイミド、Ｎ−メチルフェニルマレイミド等のＮ置換マレイミド類等を挙げることができる。なお、エチレン性不飽和単量体は、単独もしくは数種類を組み合わせることができる。 Examples of the ethylenically unsaturated monomer include methyl (meth) acrylate, n-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, and dicyclopentenyl (meth) ) Acrylate, allyl (meth) acrylate, styrene, α-methylstyrene, benzyl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-hydroxyl (Meth) ethyl acrylate and the like and their macromonomers; N such as N-methylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide and N-methylphenylmaleimide Mention may be made of the conversion maleimide, and the like. In addition, an ethylenically unsaturated monomer can be individual or can combine several types.
側鎖に水酸基及びエチレン性不飽和二重総合基を有する樹脂の水酸基価は１５ｍｇＫＯＨ／ｇ〜２００ｍｇＫＯＨ/ｇの範囲内であることが好ましく、１５ｍｇＫＯＨ／ｇ〜１５０ｍｇＫＯＨ／ｇの範囲内であることがより好ましく、２０ｍｇＫＯＨ／ｇ〜１００ｍｇＫＯＨ／ｇの範囲内であることが特に好ましい。水酸基価が１５ｍｇＫＯＨ／ｇ以上であれば、顔料誘導体中のスルホン基との相互作用が強くなり、分散液あるいは感光性赤色組成物の分散経時安定性が向上するからである。また２００ｍｇＫＯＨ/ｇ以下であれば、アルカリ現像時に露光された感光性赤色組成物塗膜が溶解することなく、所望のパターンがより好適に得られる。 The hydroxyl value of the resin having a hydroxyl group and an ethylenically unsaturated double synthetic group in the side chain is preferably in the range of 15 mgKOH / g to 200 mgKOH / g, and preferably in the range of 15 mgKOH / g to 150 mgKOH / g. More preferably, it is particularly preferably within the range of 20 mgKOH / g to 100 mgKOH / g. This is because if the hydroxyl value is 15 mg KOH / g or more, the interaction with the sulfone group in the pigment derivative becomes strong, and the dispersion aging stability of the dispersion or the photosensitive red composition is improved. Moreover, if it is 200 mgKOH / g or less, a desired pattern will be obtained more suitably, without the photosensitive red composition coating film exposed at the time of alkali image development dissolving.
また、二重結合当量は３００〜１００００の範囲内であることが好ましく、３５０〜５０００の範囲内であることがより好ましく、４００〜３０００の範囲内であることが特に好ましい。二重結合当量が３００以上であれば、二重結合量が多過ぎないので、分子量の経時的な増加が起こりにくくなりゲル化しにくくなる。また１００００以下であれば、二重結合量が少な過ぎないので、露光時の硬化不足が起こりにくくなり、アルカリ現像時に露光された感光性赤色組成物塗膜が溶解しにくくなるので、所望のパターンが得られやすくなり、得られたパターンの表面荒れも起こりにくくなるからである。 The double bond equivalent is preferably in the range of 300 to 10000, more preferably in the range of 350 to 5000, and particularly preferably in the range of 400 to 3000. If the double bond equivalent is 300 or more, the amount of double bonds is not too much, so that the molecular weight hardly increases over time and gelation is difficult. If it is 10,000 or less, the amount of double bonds is not too small, so that insufficient curing at the time of exposure hardly occurs, and the photosensitive red composition coating film exposed at the time of alkali development becomes difficult to dissolve. This is because the surface roughness of the obtained pattern is less likely to occur.
本発明のカラーフィルター用赤色感光性組成物に含まれる（Ｄ）バインダー樹脂は少なくとも上記樹脂を含むものであるが、必要に応じてその他の樹脂を含んでも良い。
このような樹脂としてはカラーフィルターに一般的に用いられるものを使用でき、具体的にはエポキシ樹脂、ウレタン樹脂、アクリル樹脂、ポリエステル樹脂、ポリイミド樹脂などの感光性、非感光性樹脂を挙げることができる。
本発明の感光性赤色組成物の固形成分中の（Ｄ）バインダー樹脂の量は５〜６０質量％が好ましく、より好ましくは、１０〜４０質量％である。上記範囲内であることにより未露光箇所における現像残渣が少なく、現像時に起こる露光箇所の表面荒れが少なく、密着性が良いものとすることができるからである。
The (D) binder resin contained in the red photosensitive composition for color filters of the present invention contains at least the above resin, but may contain other resins as necessary.
As such resins, those generally used for color filters can be used, and specific examples include photosensitive and non-photosensitive resins such as epoxy resins, urethane resins, acrylic resins, polyester resins, and polyimide resins. it can.
As for the quantity of (D) binder resin in the solid component of the photosensitive red composition of this invention, 5-60 mass% is preferable, More preferably, it is 10-40 mass%. By being within the above range, the development residue in the unexposed area is small, the surface roughness of the exposed area occurring during development is small, and the adhesion can be improved.
本発明において用いられる（Ｅ）光重合性モノマーとしては、具体的には、不飽和二重結合を有する多官能モノマーが挙げられる。
上記の多官能モノマーとしては、エチレングリコールジアクリレート、ジエチレングリコールジアクリレート、１，４−ブタンジオールジアクリレート、１，５−ペンタンジオールジアクリレート、１，６−ヘキサンジオールジアクリレート、１，３−プロパンジオールアクリレート、１，４−シクロヘキサンジオールジアクリレート、２，２−ジメチロールプロパンジアクリレート、グリセロールジアクリレート、トリプロピレングリコールジアクリレート等の二官能モノマー；グリセロールトリアクリレート、トリメチロールプロパントリアクリレート、ポリオキシエチル化トリメチロールプロパントリアクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールテトラアクリレート、トリエチレングリコールジアクリレート、ポリオキシプロピルトリメチロールプロパントリアクリレート、ブチレングリコールジアクリレート、１，２，４−ブタントリオールトリアクリレート、２，２，４−トリメチル−１，３−ペンタンジオールジアクリレート、ジアリルフマレート、１，１０−デカンジオールジメチルアクリレート、ジペンタエリスリトールペンタアクリレート、コハク酸変性ジペンタエリスリトールペンタアクリレート、ジペンタエリスリトールヘキサアクリレート等の三官能以上のモノマー、及び上記のアクリレートをメタクリレートに変えたもの、並びにγ−メタクリロキシプロピルトリメトキシシラン、１−ビニル−２−ピロリドン等が挙げられる。上記の多官能モノマーを１種又は２種以上の混合物として、あるいは、その他の化合物との混合物として、（Ｅ）光重合性モノマーに使用することができる。
以上述べた（Ｅ）光重合性モノマーは、組成物の固形成分中に５〜８０質量％程度含有されることが好ましい。
Specific examples of the (E) photopolymerizable monomer used in the present invention include polyfunctional monomers having an unsaturated double bond.
Examples of the polyfunctional monomer include ethylene glycol diacrylate, diethylene glycol diacrylate, 1,4-butanediol diacrylate, 1,5-pentanediol diacrylate, 1,6-hexanediol diacrylate, and 1,3-propanediol. Bifunctional monomers such as acrylate, 1,4-cyclohexanediol diacrylate, 2,2-dimethylolpropane diacrylate, glycerol diacrylate, tripropylene glycol diacrylate; glycerol triacrylate, trimethylolpropane triacrylate, polyoxyethylation Trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, triethylene glycol diamine , Polyoxypropyltrimethylolpropane triacrylate, butylene glycol diacrylate, 1,2,4-butanetriol triacrylate, 2,2,4-trimethyl-1,3-pentanediol diacrylate, diallyl fumarate, 1, Tri- or higher functional monomers such as 10-decanediol dimethyl acrylate, dipentaerythritol pentaacrylate, succinic acid-modified dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, and the like, and γ-methacrylate Examples include loxypropyltrimethoxysilane and 1-vinyl-2-pyrrolidone. Said polyfunctional monomer can be used for (E) a photopolymerizable monomer as a 1 type, 2 or more types of mixture, or a mixture with another compound.
The (E) photopolymerizable monomer described above is preferably contained in the solid component of the composition in an amount of about 5 to 80% by mass.
また、本発明において用いられる（Ｆ）光重合開始剤としては、具体的には、ベンゾフェノン、ミヒラーケトン（４，４'−ビスジメチルアミノベンゾフェノン）、４，４'−ビスジエチルアミノベンゾフェノン、４−メトキシ−４'−ジメチルアミノベンゾフェノン、２−エチルアントラキノン、フェナントレン等の芳香族ケトン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインフェニルエーテル等のベンゾインエーテル類、メチルベンゾイン、エチルベンゾイン等のベンゾイン、２−（ｏ−クロロフェニル）−４，５−フェニルイミダゾール２量体、２−（ｏ−クロロフェニル）−４，５−ジ（ｍ−メトキシフェニル）イミダゾール２量体、２−（ｏ−フルオロフェニル）−４，５−ジフェニルイミダゾール２量体、２−（ｏ−メトキシフェニル）−４，５−ジフェニルイミダゾール２量体、２，４，５−トリアリールイミダゾール２量体、２−（ｏ−クロロフェニル）−４，５−ジ（ｍ−メチルフェニル）イミダゾール２量体、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、２−トリクロロメチル−５−スチリル−１，３，４−オキサジアゾール、２−トリクロロメチル−５−（ｐ−シアノスチリル）−１，３，４−オキサジアゾール、２−トリクロロメチル−５−（ｐ−メトキシスチリル）−１，３，４−オキサジアゾール等のハロメチルチアゾール化合物、２，４−ビス（トリクロロメチル）−６−ｐ−メトキシスチリル−Ｓ−トリアジン、２，４−ビス（トリクロロメチル）−６−（１−ｐ−ジメチルアミノフェニル−１，３−ブタジエニル）−Ｓ−トリアジン、２−トリクロロメチル−４−アミノ−６−ｐ−メトキシスチリル−Ｓ−トリアジン、２−（ナフト−１−イル）−４，６−ビス−トリクロロメチル−Ｓ−トリアジン、２−（４−エトキシ−ナフト−１−イル）−４，６−ビス−トリクロロメチル−Ｓ−トリアジン、２−（４−ブトキシ−ナフト−１−イル）−４，６−ビス−トリクロロメチル−Ｓ−トリアジン等のハロメチル−Ｓ−トリアジン系化合物、２，２−ジメトキシ−１，２−ジフェニルエタン−１−オン、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ノン、１，２−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−１，１−ヒドロキシ−シクロヘキシル−フェニルケトン、ベンジル、ベンゾイル安息香酸、ベンゾイル安息香酸メチル、４−ベンゾイル−４´−メチルジフェニルサルファイド、ベンジルメチルケタール、ジメチルアミノベンゾエート、Ｐ−ジメチルアミノ安息香酸イソアミル、２−ｎ−ブチキシエチル−４−ジメチルアミノベンゾエート、２−クロロチオキサントン、２，４ジエチルチオキサントン、２，４ジメチルチオキサントン、イソプロピルチオキサントン、スピードキュアーＢＭＳ（ラムソン社製）、イルガキュアー１８４（チバ・スペシャルティケミカルズ社製）、イルガキュアー３６９（チバ・スペシャルティケミカルズ社製）、イルガキュアー３７９（チバ・スペシャルティケミカルズ社製）、イルガキュアー６５１（チバスペシャルティケミカルズ社製）、イルガキュアー８１９（チバスペシャルティケミカルズ社製）、イルガキュアー９０７（チバ・スペシャルティケミカルズ社製）、イルガキュアーＯＸＥ０１（チバ・スペシャルティケミカルズ社製）、イルガキュアーＯＸＥ０２（チバ・スペシャルティケミカルズ社製）、ダロキュアーＴＰＯ（チバ・スペシャルティケミカルズ社製）等の光重合開始剤が挙げられる。本発明では、これらの光重合開始剤を単独で、又は、２種以上を混合して使用することができる。
本発明の感光性赤色組成物固形成分中の、（Ｆ）光重合開始剤の使用量としては、３〜４０質量％、特に５〜１５質量％の範囲内であることが好ましい。
Specific examples of the photopolymerization initiator (F) used in the present invention include benzophenone, Michler's ketone (4,4′-bisdimethylaminobenzophenone), 4,4′-bisdiethylaminobenzophenone, 4-methoxy- Aromatic ketones such as 4′-dimethylaminobenzophenone, 2-ethylanthraquinone and phenanthrene, benzoin ethers such as benzoin methyl ether, benzoin ethyl ether and benzoin phenyl ether, benzoin such as methyl benzoin and ethyl benzoin, Chlorophenyl) -4,5-phenylimidazole dimer, 2- (o-chlorophenyl) -4,5-di (m-methoxyphenyl) imidazole dimer, 2- (o-fluorophenyl) -4,5- Diphenylimidazole dimer, 2 (O-methoxyphenyl) -4,5-diphenylimidazole dimer, 2,4,5-triarylimidazole dimer, 2- (o-chlorophenyl) -4,5-di (m-methylphenyl) imidazole Dimer, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone, 2-trichloromethyl-5-styryl-1,3,4-oxadiazole, 2-trichloromethyl-5 Halomethylthiazole compounds such as-(p-cyanostyryl) -1,3,4-oxadiazole, 2-trichloromethyl-5- (p-methoxystyryl) -1,3,4-oxadiazole, 2, 4-bis (trichloromethyl) -6-p-methoxystyryl-S-triazine, 2,4-bis (trichloromethyl) -6- (1-p-dimethylaminophenyl) Nyl-1,3-butadienyl) -S-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-S-triazine, 2- (naphth-1-yl) -4,6-bis-trichloro Methyl-S-triazine, 2- (4-ethoxy-naphth-1-yl) -4,6-bis-trichloromethyl-S-triazine, 2- (4-butoxy-naphth-1-yl) -4,6 -Halomethyl-S-triazine compounds such as bis-trichloromethyl-S-triazine, 2,2-dimethoxy-1,2-diphenylethane-1-one, 2-methyl-1- [4- (methylthio) phenyl] 2-morpholinopropanone, 1,2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,1-hydroxy-cyclohexyl-pheni Luketone, benzyl, benzoylbenzoic acid, methyl benzoylbenzoate, 4-benzoyl-4'-methyldiphenyl sulfide, benzylmethyl ketal, dimethylaminobenzoate, isoamyl P-dimethylaminobenzoate, 2-n-butoxyethyl-4-dimethylamino Benzoate, 2-chlorothioxanthone, 2,4 diethylthioxanthone, 2,4 dimethylthioxanthone, isopropylthioxanthone, Speed Cure BMS (Lambson), Irgacure 184 (Ciba Specialty Chemicals), Irgacure 369 (Ciba Specialty) Chemicals), Irgacure 379 (Ciba Specialty Chemicals), Irgacure 651 (Ciba Specialty Chemicals), Irgacure -819 (Ciba Specialty Chemicals), Irgacure 907 (Ciba Specialty Chemicals), Irgacure OXE01 (Ciba Specialty Chemicals), Irgacure OXE02 (Ciba Specialty Chemicals), Darocur TPO (Ciba) -Photopolymerization initiators such as Specialty Chemicals). In this invention, these photoinitiators can be used individually or in mixture of 2 or more types.
The amount of the photopolymerization initiator (F) used in the solid component of the photosensitive red composition of the present invention is preferably in the range of 3 to 40% by mass, particularly 5 to 15% by mass.
また、上記の（Ｆ）光重合開始剤と併用して、水素供与体として、脂肪族あるいは芳香族の単、多官能チオール化合物や芳香族アミン系化合物を用いることができる。本発明の感光性赤色組成物固形成分中の、上記の水素供与体の使用量としては、０．５〜３０質量％、特に２〜２０質量％の範囲内であることが好ましい。 Further, in combination with the above (F) photopolymerization initiator, an aliphatic or aromatic mono- or polyfunctional thiol compound or an aromatic amine compound can be used as a hydrogen donor. The amount of the hydrogen donor used in the solid component of the photosensitive red composition of the present invention is preferably 0.5 to 30% by mass, particularly preferably 2 to 20% by mass.
本発明において用いられる（Ｇ）溶剤としては、一般的にカラーフィルター用感光性赤色組成物に使用されているものであれば特に限定されるものではない。具体的には、エチレングリコールモノメチルエーテル、エチ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モノメチルエーテル、ジエチレングリコールモノエチルエーテル、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、ジプロピレングリコールジメチルエーテル等の（モノあるいはポリ）アルキレングリコール（モノあるいはポリ）アルキルエーテル類、及びこれらのアセテート類；プロピレングリコールジアセテート、１，３−ブチレングリコールジアセテート等のジアセテート類；テトラヒドロフラン等のエーテル類；メチルエチルケトン、シクロヘキサノン、２−ヘプタノン等のケトン類；２−ヒドロキシプロピオン酸メチル、３−ヒドロキシプロピオン酸エチル、酢酸エチル、ｎ−ブチルアセテート、ｉ−ブチルアセテート、酪酸ｉ−ブチル、酪酸ｎ−ブチル、３−メトキシプロピオン酸エチル、３−エトキシプロピオン酸エチル、３−メトキシブチルアセテート、３−メチル−３−メトキシブチルアセテート、乳酸エチル、シクロヘキサノールアセテート等のエステル類；トルエン、キシレン等の芳香族炭化水素類等を挙げることができる。これらの溶剤のうち、プロピレングリコールモノメチルエーテルアセテート、３−メトキシブチルアセテート、エチレングリコールモノメチルエーテル、ジエチレングリコールジエチルエーテル等が溶解性、顔料分散性、塗布性の観点から好ましい。なお、上記溶剤は、単独で又は２種以上を混合して使用することができる。
本発明の感光性赤色組成物全量中の、（Ｇ）溶剤量としては、好ましくは５０〜９０質量％、特に好ましくは６０〜８５質量％である。
The (G) solvent used in the present invention is not particularly limited as long as it is generally used in a photosensitive red composition for a color filter. Specifically, (mono or poly) alkylene glycol (mono or poly) such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and dipropylene glycol dimethyl ether. ) Alkyl ethers and their acetates; diacetates such as propylene glycol diacetate and 1,3-butylene glycol diacetate; ethers such as tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone and 2-heptanone; Methyl hydroxypropionate, ethyl 3-hydroxypropionate, ethyl acetate, n Butyl acetate, i-butyl acetate, i-butyl butyrate, n-butyl butyrate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, ethyl lactate And esters such as cyclohexanol acetate; aromatic hydrocarbons such as toluene and xylene. Of these solvents, propylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, ethylene glycol monomethyl ether, diethylene glycol diethyl ether, and the like are preferable from the viewpoints of solubility, pigment dispersibility, and coatability. In addition, the said solvent can be used individually or in mixture of 2 or more types.
The amount of the solvent (G) in the total amount of the photosensitive red composition of the present invention is preferably 50 to 90% by mass, particularly preferably 60 to 85% by mass.
また、本発明のカラーフィルター用感光性赤色組成物には、添加剤として、増感剤、重合停止剤、連鎖移動剤、レベリング剤、可塑剤、シランカップリング剤、界面活性剤、消泡剤等が必要に応じて用いられる。
本発明において用いることができる界面活性剤としては、例えば、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンオクチルフェニルエーテル、ポリオキシエチレンノニルフェニルエーテル、ポリエチレングリコールジラウレート、ポリエチレングリコールジステアレート、ソルビタン脂肪酸エステル類、脂肪酸変性ポリエステル類、３級アミン変性ポリウレタン類等を挙げることができる。
本発明の感光性赤色組成物は通常、紫外線照射や可視光線照射により硬化するが、紫外線照射による硬化が好ましい。
The photosensitive red composition for color filters of the present invention includes, as additives, a sensitizer, a polymerization terminator, a chain transfer agent, a leveling agent, a plasticizer, a silane coupling agent, a surfactant, and an antifoaming agent. Etc. are used as necessary.
Examples of the surfactant that can be used in the present invention include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene nonyl phenyl ether, and polyethylene glycol dilaurate. , Polyethylene glycol distearate, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, and the like.
The photosensitive red composition of the present invention is usually cured by ultraviolet irradiation or visible light irradiation, but curing by ultraviolet irradiation is preferred.
上記のように調製された本発明の感光性赤色組成物は、例えば、これを用いて、遮光層がパターン形成されたカラーフィルター用のガラス基板に回転塗布（スピンコート）、流延塗布、浸漬塗布、ロール塗布、特にダイコート法等の公知の塗布方法により塗布し、真空度が０．１〜１．０ｔｏｒｒ程度、例えば０．２ｔｏｒｒに到達するまで真空ベイクを行って０．５〜４μｍ程度（乾燥膜厚）の塗布膜を得る。得られた塗布膜に目的の画素を形成するためのネガ型のフォトマスクを介して高圧水銀灯や超高圧水銀灯等により１０〜５００ｍJ／ｃｍ2 程度の光量の紫外線を照射し露光する。露光後、光硬化した塗膜を公知のアルカリ現像液を使用してスプレイ法や浸漬法にて現像し、未露光部を溶解して目的とする色に相当する画素を得る。必要に応じて、現像後、２００〜２５０℃程度の温度で１０〜６０分程度、後硬化処理（ポストベイク）することができる。上記の画素を得る工程を、カラーフィルターに必要とされる色の数だけ繰り返すことによって目的とするカラーフィルターが得られる。上記のカラーフィルターは、赤の画素のみを有する赤色カラーフィルターとして製造しても良いが、通常、本発明の感光性赤色組成物を用いて形成する赤の画素のほか、緑及び青の各画素を遮光層がパターン形成されたカラーフィルター用のガラス基板上に配置したものが製造される。 The photosensitive red composition of the present invention prepared as described above is used, for example, for spin coating, casting coating, and dipping on a glass substrate for a color filter having a light shielding layer patterned. Coating is performed by a known coating method such as coating, roll coating, especially die coating, and vacuum baking is performed until the degree of vacuum reaches about 0.1 to 1.0 torr, for example, 0.2 torr, and about 0.5 to 4 μm ( A coating film having a dry film thickness is obtained. The obtained coating film is exposed by irradiating it with ultraviolet light having a light amount of about 10 to 500 mJ / cm 2 by a high pressure mercury lamp, an ultrahigh pressure mercury lamp or the like through a negative photomask for forming a target pixel. After the exposure, the photocured coating film is developed by a spray method or a dipping method using a known alkaline developer, and the unexposed portion is dissolved to obtain a pixel corresponding to the target color. If necessary, after development, post-curing can be performed at a temperature of about 200 to 250 ° C. for about 10 to 60 minutes. A target color filter can be obtained by repeating the above-described step of obtaining the pixels by the number of colors required for the color filter. The above color filter may be manufactured as a red color filter having only red pixels. Usually, in addition to the red pixels formed using the photosensitive red composition of the present invention, each of the green and blue pixels. Are arranged on a glass substrate for a color filter on which a light shielding layer is patterned.
以上のように製造したカラーフィルターは、Ｃ光源及び２°視野の条件において、ＸＹＺ表色系色度図における色度座標（ｘ，ｙ）が以下の範囲にあることが好ましい。
０．５４０≦ｘ≦０．６７０
０．３３６≦ｙ≦０．３４９
この範囲に色度座標（ｘ，ｙ）があれば、赤色画素の色調が黄色やオレンジ色に偏ることなく、且つ高透過率が実現できる。
The color filter manufactured as described above preferably has chromaticity coordinates (x, y) in the XYZ color system chromaticity diagram in the following range under the condition of a C light source and a 2 ° visual field.
0.540 ≦ x ≦ 0.670
0.336 ≦ y ≦ 0.349
If the chromaticity coordinates (x, y) are in this range, the color tone of the red pixel is not biased to yellow or orange, and high transmittance can be realized.
本発明を実施例により、さらに詳細に説明するが、本発明は、これらの例によってなんら限定されるものではない。
なお、感光性赤色組成物の分散性、色度ｘ、色度ｙ及び輝度Ｙは、下記の方法に従って評価した。
＜分散性＞
東機産業（株）製Ｂ型粘度計を用い、回転数６０ｒｐｍにて粘度変化比｛粘度変化比＝（１０日後の粘度）／（初期粘度）｝を測定し、下記基準により評価した。
○： 感光性赤色組成物の粘度変化が少なく、上記粘度変化比が１．５未満である。
×： 感光性赤色組成物の粘度変化が大きく、上記粘度変化比が１．５以上である。
＜色度ｘ、色度ｙ及び輝度Ｙ＞
オリンパス（株）製 ＯＳＰ−ＳＰ２００顕微分光測光装置を用いて、ＪＩＳ Ｚ８７０１に定める色度ｘ、色度ｙ及びＸＹＺ表色系における三刺激値のＹ（明るさＹ）値を輝度Ｙとして測定した。測定条件は、光源がＣ光源、照明倍率２０倍、ピンホールＮｏ．７（５０μｍ）である。
Examples The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
The dispersibility, chromaticity x, chromaticity y, and luminance Y of the photosensitive red composition were evaluated according to the following methods.
<Dispersibility>
Using a B-type viscometer manufactured by Toki Sangyo Co., Ltd., the viscosity change ratio {viscosity change ratio = (viscosity after 10 days) / (initial viscosity)} was measured at a rotational speed of 60 rpm, and evaluated according to the following criteria.
A: The viscosity change of the photosensitive red composition is small, and the viscosity change ratio is less than 1.5.
X: The viscosity change of the photosensitive red composition is large, and the viscosity change ratio is 1.5 or more.
<Chromaticity x, chromaticity y, and luminance Y>
Using an Olympus Co., Ltd. OSP-SP200 microspectrophotometer, the chromaticity x, chromaticity y and tristimulus Y (brightness Y) values defined in JIS Z8701 were measured as luminance Y. . The measurement conditions were as follows: the light source was a C light source, the illumination magnification was 20 times, and the pinhole no. 7 (50 μm).
製造例１ 顔料誘導体の調製
６０ｇのＰＯ３８（NOVOPERM RED HFG、Clariant社製）を撹拌しながら９０℃で発煙硫酸（２８％ＳＯ3）８００ｇ中に投入した。３時間撹拌した後、氷水１５００ｇ中に注ぎ入れた。３０分間放置後、生じた懸濁液を濾過し、得られた生成物を３００ｍｌの純水で洗浄した。純水２０００ｍｌ中へ前記生成物を投入し、アンモニア水溶液でｐＨが７以上になるまでアンモニア水溶液を添加し、中和を行い、次いで濾過を行った。得られたウェット結晶を純水で洗浄した後、８０℃で乾燥した。乾燥して得られたものを純水による洗浄、濾過、乾燥という操作を１０回繰り返して、６２ｇのＰＯ３８から得られるスルホン酸基を有する化合物である顔料誘導体を得た。
Production Example 1 Preparation of Pigment Derivative 60 g of PO38 (NOVOPERM RED HFG, manufactured by Clariant) was added to 800 g of fuming sulfuric acid (28% SO 3 ) at 90 ° C. with stirring. After stirring for 3 hours, the mixture was poured into 1500 g of ice water. After standing for 30 minutes, the resulting suspension was filtered, and the resulting product was washed with 300 ml of pure water. The product was put into 2000 ml of pure water, an aqueous ammonia solution was added until the pH reached 7 or more with an aqueous ammonia solution, neutralized, and then filtered. The obtained wet crystals were washed with pure water and then dried at 80 ° C. Operations obtained by drying, washing with pure water, filtering, and drying were repeated 10 times to obtain a pigment derivative that is a compound having a sulfonic acid group obtained from 62 g of PO38.
製造例２ バインダー樹脂：側鎖に水酸基及びエチレン性不飽和二重結合基を有する樹脂の調製
ベンジルメタクリレート３０ｇ（０．１７モル）、メタクリル酸メチル３８ｇ（０．３８モル）、メタクリル酸１８ｇ（０．２１モル）及びｔ−ブチル−オキシ−２−エチルヘキサノエート（商品名パーブチルＯ、日本油脂社製）１０ｇの混合液を、プロピレングリコールモノメチルエーテルアセテート１５０ｇを入れた重合槽中に、窒素気流下１００℃で、３時間かけて滴下した。
滴下終了後、さらに３時間加熱することにより重合体溶液を得た。この重合体溶液の重量平均分子量（Ｍｗ）はポリスチレン換算で８，０００であった。
次に、得られた重合体溶液に、グリシジルメタクリレート１４ｇ（０．１０モル）、トリエチルアミン０．２ｇ及びｐ−メトキシフェノール０．０５ｇを添加し、１１０℃で１０時間加熱することにより主鎖メタクリル酸のカルボン酸基とグリシジルメタクリレートのエポキシ基との反応を行なった。反応中は、グリシジルメタクリレートの重合を防ぐため、反応溶液内に空気をバブリングさせた。反応は、溶液の水酸基価測定により追跡した。得られた反応溶液は固形分（ＮＶ）４０質量％、水酸基価７５ｍｇＫＯＨ／ｇであり、重量平均分子量（Ｍｗ）は１０，０００、二重結合当量は１０１４であった。
Production Example 2 Binder resin: Preparation of a resin having a hydroxyl group and an ethylenically unsaturated double bond group in the side chain 30 g (0.17 mol) of benzyl methacrylate, 38 g (0.38 mol) of methyl methacrylate, 18 g of methacrylic acid (0 .21 mol) and 10 g of t-butyl-oxy-2-ethylhexanoate (trade name Perbutyl O, manufactured by NOF Corporation) in a polymerization tank containing 150 g of propylene glycol monomethyl ether acetate It was added dropwise at 100 ° C. over 3 hours.
After completion of the dropwise addition, the polymer solution was obtained by further heating for 3 hours. The weight average molecular weight (Mw) of this polymer solution was 8,000 in terms of polystyrene.
Next, 14 g (0.10 mol) of glycidyl methacrylate, 0.2 g of triethylamine and 0.05 g of p-methoxyphenol were added to the obtained polymer solution, and the main chain methacrylic acid was heated by heating at 110 ° C. for 10 hours. The reaction between the carboxylic acid group of glycidyl methacrylate and the epoxy group of glycidyl methacrylate was carried out. During the reaction, air was bubbled into the reaction solution in order to prevent polymerization of glycidyl methacrylate. The reaction was followed by measuring the hydroxyl value of the solution. The obtained reaction solution had a solid content (NV) of 40% by mass, a hydroxyl value of 75 mgKOH / g, a weight average molecular weight (Mw) of 10,000, and a double bond equivalent of 1014.
重量平均分子量（Ｍｗ）は、ゲル・パーミエーション・クロマトグラフィー（ＧＰＣ）により標準ポリスチレン換算値として求めた。
水酸基価はＪＩＳ Ｋ００７０に従って測定した後、固形分濃度から固形分１ｇ当りの水酸基価を算出した。
二重結合当量は、バインダー樹脂における二重結合１個当りの重量平均分子量のことであり、下記の式により算出することができる。
二重結合当量＝（配合した単量体の総質量）／｛（配合した単量体において分子内にエポキシ基とエチレン性不飽和基を持つ化合物のモル数）×（分子内にエポキシ基とエチレン性不飽和基を持つ化合物中のエチレン性不飽和基の数）｝
The weight average molecular weight (Mw) was determined as a standard polystyrene equivalent value by gel permeation chromatography (GPC).
The hydroxyl value was measured according to JIS K0070, and the hydroxyl value per gram of the solid content was calculated from the solid content concentration.
The double bond equivalent is a weight average molecular weight per double bond in the binder resin, and can be calculated by the following formula.
Double bond equivalent = (total mass of blended monomer) / {(number of moles of compound having epoxy group and ethylenically unsaturated group in molecule in blended monomer) × (epoxy group in molecule) Number of ethylenically unsaturated groups in compounds with ethylenically unsaturated groups)}
製造例３〜９ 顔料分散液Ａｌ〜Ａ７の調製
表１に示す配合組成によりペイントシェーカーにて（０．３ｍｍジルコニアビーズ、３時間）分散し、顔料分散液Ａｌ〜Ａ７を調製した。
Production Examples 3 to 9 Preparation of Pigment Dispersions Al to A7 Pigment dispersions Al to A7 were prepared by dispersing with a paint shaker (0.3 mm zirconia beads, 3 hours) according to the formulation shown in Table 1.
ＰＯ３８： 商品名「NOVOPERM RED HFG」（Clariant社製）
ＰＲ２５４： 商品名「IRGAPHOR RED BT-CF」（チバ・スペシャルティー・ケミカルズ社製）
ＰＹ１３９： 商品名「IRGAPHOR YELLOW 2R-CF」（チバ・スペシャルティー・ケミカルズ社製）
顔料誘導体： 製造例１で得られた顔料誘導体
分散剤１： 商品名「Disperbyk-161」（アミン価：３６．６ｍｇＫＯＨ／ｇ、固形分３０質量％、ビックケミー社製）
分散剤２： 商品名「Disperbyk-103」（アミン価：０ｍｇＫＯＨ／ｇ、固形分４０質量％、ビックケミー社製）
分散剤３： 商品名「Disperbyk-130」（アミン価：３７２．５ｍｇＫＯＨ／ｇ、固形分５１質量％、ビックケミー社製）
バインダー樹脂：製造例２で得られた側鎖に水酸基及びエチレン性不飽和二重結合基を有する樹脂（固形分４０質量％）
溶剤：プロピレングリコールモノメチルエーテルアセテート
PO38: Product name “NOVOPERM RED HFG” (manufactured by Clariant)
PR254: Product name “IRGAPHOR RED BT-CF” (Ciba Specialty Chemicals)
PY139: Product name "IRGAPHOR YELLOW 2R-CF" (Ciba Specialty Chemicals)
Pigment derivative: Pigment derivative dispersant obtained in Production Example 1: Trade name “Disperbyk-161” (amine value: 36.6 mg KOH / g, solid content 30% by mass, manufactured by Big Chemie)
Dispersant 2: Trade name “Disperbyk-103” (Amine value: 0 mg KOH / g, solid content 40% by mass, manufactured by Big Chemie)
Dispersant 3: Trade name “Disperbyk-130” (amine value: 372.5 mg KOH / g, solid content 51 mass%, manufactured by Big Chemie)
Binder resin: Resin having a hydroxyl group and an ethylenically unsaturated double bond group in the side chain obtained in Production Example 2 (solid content: 40% by mass)
Solvent: Propylene glycol monomethyl ether acetate
実施例１及び比較例１〜６
製造例３〜９で得られた顔料分散液Ａｌ〜Ａ７を用いて、表２に示す配合組成にて、ディゾルバーを用いて１時間撹拌し、実施例１及び比較例１〜６のネガ型感光性赤色組成物を調製した。得られた各感光性赤色組成物の分散性を上記の方法により評価した。評価結果を表２に示す。
Example 1 and Comparative Examples 1-6
Using the pigment dispersions Al to A7 obtained in Production Examples 3 to 9, the mixture composition shown in Table 2 was stirred for 1 hour using a dissolver, and negative photosensitive materials of Example 1 and Comparative Examples 1 to 6 were used. Red composition was prepared. The dispersibility of each photosensitive red composition obtained was evaluated by the above method. The evaluation results are shown in Table 2.
顔料分散液： 製造例３〜９で得られた顔料分散液Ａ−１〜Ａ−７
バインダー樹脂： 製造例２で得られた側鎖に水酸基及びエチレン性不飽和二重結合基を有する樹脂（固形分４０質量％）
光重合性モノマー： ジペンタエリスリトールヘキサアクリレート（ＤＰＨＡ）
光重合開始剤： ２−ベンジル−２−ジメチルアミノ−１−（４−モルホリノフェニル）ブタン−１−オン（商品名イルガキュアー３６９、チバ・スペシャルティー・ケミカルズ社製）
溶剤： プロピレングリコールモノメチルエーテルアセテート（ＰＧＭＥＡ）
Pigment dispersion: Pigment dispersions A-1 to A-7 obtained in Production Examples 3 to 9
Binder resin: Resin having a hydroxyl group and an ethylenically unsaturated double bond group in the side chain obtained in Production Example 2 (solid content: 40% by mass)
Photopolymerizable monomer: Dipentaerythritol hexaacrylate (DPHA)
Photopolymerization initiator: 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one (trade name Irgacure 369, manufactured by Ciba Specialty Chemicals)
Solvent: Propylene glycol monomethyl ether acetate (PGMEA)
次に、透明ガラス基版上に上記の実施例１及び比較例１で得られた各感光性赤色組成物をスピンコーターで塗布し、その後、８０℃中ホットプレートにて、３分間加熱処理（プレベイク）することにより、感光性赤色組成物塗膜を得た。なお、感光性赤色組成物の塗布は、スピンコーター回転数を調整して、パターンの色度がＣ光源でｘ＝０．５８８、ｙ＝０．３４３になるように調整した。次にプロキシ露光機にてクロムマスクを介し、露光ギャップ１５０μｍ、超高圧水銀灯でｉ線換算６０ｍｊの光量で所定領域を露光し、次に、０．０５％の水酸化カリウム水溶液（任意で界面活性剤添加有り）でアルカリ現像を行ない、続いて純水洗浄を行なうことにより、パターニング基板を得た。得られたパターニング基板を熱風オーブン中２３０℃で、３０分問保持することにより、アクリル系樹脂の硬化を行なった。以上より、赤色画素を形成した基板を作製した。
上記の基板を使用し、色度ｘ、色度ｙ及び輝度Ｙに関して上記の測定方法により評価した。評価結果を表２に示す。なお、分散性の悪い比較例２〜６の感光性赤色組成物は、感光性赤色組成物塗膜を得るに至らず、色度ｘ、色度ｙ及び輝度Ｙを測定できなかった。
Next, each photosensitive red composition obtained in Example 1 and Comparative Example 1 was applied on a transparent glass base plate with a spin coater, and then heat-treated for 3 minutes on a hot plate at 80 ° C. ( By prebaking, a photosensitive red composition coating film was obtained. The photosensitive red composition was applied by adjusting the spin coater rotation speed so that the chromaticity of the pattern was x = 0.588 and y = 0.343 with a C light source. Next, a proxy exposure machine is used to expose a predetermined area through a chromium mask with an exposure gap of 150 μm and an ultrahigh pressure mercury lamp with an amount of i-converted 60 mj, and then 0.05% potassium hydroxide aqueous solution (optionally surface active) Alkali development was performed with the addition of an agent, followed by pure water cleaning to obtain a patterned substrate. The obtained patterned substrate was held in a hot air oven at 230 ° C. for 30 minutes to cure the acrylic resin. As described above, a substrate on which red pixels were formed was produced.
Using the above substrate, the chromaticity x, chromaticity y and luminance Y were evaluated by the above measuring method. The evaluation results are shown in Table 2. In addition, the photosensitive red composition of Comparative Examples 2-6 with a bad dispersibility did not reach the photosensitive red composition coating film, but was not able to measure chromaticity x, chromaticity y, and the brightness | luminance Y.
表２から明らかなように、本発明の実施例１の感光性赤色組成物は、比較例１の感光性赤色組成物と同等の分散性を得ることができ、輝度Ｙも比較例１と比較して大幅に良好であり、高透過率及び高コントラストを実現できた。比較例２〜６の感光性赤色組成物は、いずれも分散安定性が悪く、分散直後から著しい増粘を起こすためスピンコート等で塗布した際に均一な赤色組成物塗膜が形成できず、使用に耐えるものではなかった。 As is clear from Table 2, the photosensitive red composition of Example 1 of the present invention can obtain the same dispersibility as the photosensitive red composition of Comparative Example 1, and the luminance Y is also compared with Comparative Example 1. Thus, it was significantly better, and high transmittance and high contrast could be realized. The photosensitive red compositions of Comparative Examples 2 to 6 are all poor in dispersion stability and cannot form a uniform red composition coating film when applied by spin coating or the like because of significant increase in viscosity immediately after dispersion. It did not endure use.
本発明の感光性赤色組成物は、カラーフィルターに好適に用いられ、それを有するカラーフィルターは、テレビジョン等に用いられる高精細なカラーフィルター、特に、大型テレビジョン等の液晶表示装置の大型ガラス基板を有するカラーフィルターとして好適に用いられる。 The photosensitive red composition of the present invention is suitably used for a color filter, and the color filter having the photosensitive red composition is a high-definition color filter used for a television or the like, particularly a large glass of a liquid crystal display device such as a large television. It is suitably used as a color filter having a substrate.
Claims (3)
０．５４０≦ｘ≦０．６７０
０．３３６≦ｙ≦０．３４９ The color filter according to claim 2, wherein the chromaticity coordinates (x, y) in the XYZ color system chromaticity diagram are in the following range under the condition of a C light source and a 2 ° visual field.
0.540 ≦ x ≦ 0.670
0.336 ≦ y ≦ 0.349
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|---|---|---|---|---|
| JP2013195941A (en) * | 2012-03-22 | 2013-09-30 | Toyo Ink Sc Holdings Co Ltd | Red coloring composition for color filter, and color filter |
| KR20130129853A (en) * | 2012-05-21 | 2013-11-29 | 토요잉크Sc홀딩스주식회사 | Pigment composition, its manufacturing method, coloring composition, and color filter |
| JP2014067024A (en) * | 2012-09-10 | 2014-04-17 | Toyo Ink Sc Holdings Co Ltd | Red coloring composition for color filter, and color filter |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108473611A (en) | 2016-03-29 | 2018-08-31 | 株式会社艾迪科 | Photosensitive composite |
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| JP2013195941A (en) * | 2012-03-22 | 2013-09-30 | Toyo Ink Sc Holdings Co Ltd | Red coloring composition for color filter, and color filter |
| KR20130129853A (en) * | 2012-05-21 | 2013-11-29 | 토요잉크Sc홀딩스주식회사 | Pigment composition, its manufacturing method, coloring composition, and color filter |
| KR102116437B1 (en) * | 2012-05-21 | 2020-05-29 | 토요잉크Sc홀딩스주식회사 | Pigment composition, its manufacturing method, coloring composition, and color filter |
| JP2014067024A (en) * | 2012-09-10 | 2014-04-17 | Toyo Ink Sc Holdings Co Ltd | Red coloring composition for color filter, and color filter |
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