JP6645859B2 - Green pigment dispersion for color filters - Google Patents

Green pigment dispersion for color filters Download PDF

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JP6645859B2
JP6645859B2 JP2016021259A JP2016021259A JP6645859B2 JP 6645859 B2 JP6645859 B2 JP 6645859B2 JP 2016021259 A JP2016021259 A JP 2016021259A JP 2016021259 A JP2016021259 A JP 2016021259A JP 6645859 B2 JP6645859 B2 JP 6645859B2
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pigment
green
color filter
yellow
dispersion
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JP2017138561A (en
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林 明
明 林
平井 淳一
淳一 平井
俊輔 杉江
俊輔 杉江
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Sakata Inx Corp
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Priority to KR1020160174229A priority patent/KR102664035B1/en
Priority to TW105142837A priority patent/TWI710605B/en
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084Dispersions of dyes
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/20Filters
    • G02B5/22Absorbing filters
    • G02B5/223Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1335Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509Filters, e.g. light shielding masks
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1335Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509Filters, e.g. light shielding masks
    • G02F1/133514Colour filters
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007Filters, e.g. additive colour filters; Components for display devices
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/09Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Optics & Photonics (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Mathematical Physics (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Optical Filters (AREA)
  • Materials For Photolithography (AREA)

Description

本発明は、主に透過型または反射型カラー液晶ディスプレイに使用される光学的カラーフィルターの製造に使用される緑色顔料分散物及び緑色着色組成物に関する。   The present invention relates to a green pigment dispersion and a green coloring composition mainly used for producing an optical color filter used for a transmission type or reflection type color liquid crystal display.

カラーフィルターは、ガラス等の透明な基板の表面に2種以上の異なる色相の微細な帯(ストライプ)を平行に配置したもの、或は微細な画素を縦横一定の配列に配置したものからなっている。画素サイズは、数10〜数100μmという微細な形状であり、しかも色相毎に所定の順序で整然と配列される。このため、カラーフィルターの製造方法については、種々の方法が提案されている。   A color filter is formed by arranging two or more kinds of fine bands (stripe) of different hues in parallel on the surface of a transparent substrate such as glass, or by arranging fine pixels in a fixed arrangement in vertical and horizontal directions. I have. The pixel size has a fine shape of several tens to several hundreds μm, and is arranged in a predetermined order for each hue. For this reason, various methods have been proposed for producing color filters.

カラーフィルターは高い透明性が必要とされるため、従来、ゼラチン、カゼイン等の染色可能な天然高分子の水溶液に、重クロム酸等の感光剤を加えて感光化し、フォトリソグラフィー法を用いて画素パターンを形成し、上記画素パターンを所望の色に染色して色パターンを得る工程を3回繰り返して3色の透明着色微細パターンを形成する、いわゆる染色法を用いることにより製造されていた。   Since color filters require high transparency, conventionally, a photosensitizer such as dichromic acid is added to an aqueous solution of a dyeable natural polymer such as gelatin or casein to sensitize it, and the pixels are formed using photolithography. The process of forming a pattern and dyeing the pixel pattern into a desired color to obtain a color pattern is repeated three times to form a transparent colored fine pattern of three colors, that is, by using a so-called dyeing method.

近年、カラー液晶ディスプレイパネルの大型化、用途の多様化に伴い、耐熱性、耐光性といった信頼性向上の要求がなされるようになってきた。   In recent years, with the enlargement of color liquid crystal display panels and diversification of applications, demands for improvement in reliability such as heat resistance and light resistance have been made.

この要求に対し、カラーフィルター形成用の色材として、色特性に優れるものの耐熱性や耐光性に限界がある染料のかわりに、耐光性及び耐熱性に優れる有機顔料が用いられるようになった。   In response to this demand, organic pigments having excellent light resistance and heat resistance have been used instead of dyes having excellent color characteristics but having limited heat resistance and light resistance as coloring materials for forming color filters.

有機顔料を分散した感放射線性着色樹脂組成物を用いてカラーフィルターを製造するに当たっては、透明基板上あるいは予め所望のパターンの遮光層を形成した基板上に、有機顔料を分散した感放射線性着色樹脂組成物を塗布、乾燥した後、乾燥した塗膜を所望のパターンに露光、現像することにより、各色の画素を得ている。   In producing a color filter using a radiation-sensitive colored resin composition in which an organic pigment is dispersed, a radiation-sensitive coloring in which an organic pigment is dispersed on a transparent substrate or a substrate on which a light-shielding layer having a desired pattern has been formed in advance. After applying and drying the resin composition, the dried coating film is exposed to a desired pattern and developed to obtain pixels of each color.

しかし、有機顔料を分散した感放射線性着色樹脂組成物を用いる場合、例えば、透明基板上にブルー、グリーン、レッドの光の3原色を配列してなるカラーフィルターにおいては、一般に、単一の顔料だけでは、それぞれのカラーフィルターとしての分光スペクトルを得るのは困難であり、顔料を2種以上用いて調製することが必要とされる。   However, when a radiation-sensitive colored resin composition in which an organic pigment is dispersed is used, for example, in a color filter in which three primary colors of blue, green, and red light are arranged on a transparent substrate, a single pigment is generally used. It is difficult to obtain a spectral spectrum as each color filter by using only the pigment, and it is necessary to prepare a pigment using two or more kinds.

緑色カラーフィルターについては、特許文献1〜3等に記載されているように一般的に、C.I.ピグメントグリーン7、36、58等の緑色顔料に、C.I.ピグメントイエロー139、17、128、150、155、185等のイエロー顔料を加えスペクトル及び明度を調整している。   As for the green color filter, C.I. I. Green pigments such as CI Pigment Green 7, 36 and 58; I. A yellow pigment such as CI Pigment Yellow 139, 17, 128, 150, 155, 185 is added to adjust the spectrum and lightness.

しかしながら、透過率、すなわち明度を高め、また色純度を上げるなど、カラーフィルターに対する色特性の要求が高まるなか、これらの顔料種の組合せだけではカラーフィルターとしての色特性の向上に限界があった。   However, as the demand for color characteristics for a color filter increases, such as increasing the transmittance, that is, the lightness and the color purity, there is a limit to the improvement of the color characteristics as a color filter only by the combination of these pigment types.

色特性に優れる緑色顔料としてはC.I.ピグメントグリーン59があるが、顔料分散液の作成が技術的に困難であるため、これまで実用化されていない。   Green pigments having excellent color characteristics include C.I. There is I. Pigment Green 59, but it has not been practically used until now because preparation of a pigment dispersion is technically difficult.

特開平10−237325号公報JP-A-10-237325 特開平11−14825号公報JP-A-11-14825 特開2014−2314号公報JP 2014-2314 A

本発明の課題は、前記従来技術の課題に鑑み、色特性に優れるカラーフィルター用緑色顔料分散物を提供することにある。   An object of the present invention is to provide a green pigment dispersion for a color filter having excellent color characteristics in view of the above-mentioned problems of the related art.

本発明者らは、かかる課題を解決するために、緑色顔料、必要により黄色顔料との組み合わせ、ならびにこれらを微細に分散させる顔料分散剤について種々検討を行った結果、緑の主顔料、調色顔料としての黄色顔料、顔料を微細に分散させる顔料分散剤として特定のものを組合わせることにより、上記の課題を解決できることを見出し、本発明を完成するに至った。   The present inventors have conducted various studies on a green pigment, a combination with a yellow pigment as necessary, and a pigment dispersant for finely dispersing these, in order to solve such a problem. The inventors have found that the above problems can be solved by combining a yellow pigment as a pigment and a specific pigment dispersant for finely dispersing the pigment, and have completed the present invention.

すなわち、本発明は、(1)顔料、顔料分散剤および溶剤を含むカラーフィルター用緑色顔料分散物において、顔料としてC.I.ピグメントグリーン59を含むカラーフィルター用緑色顔料分散物に関する。   That is, the present invention relates to (1) a green pigment dispersion for a color filter containing a pigment, a pigment dispersant and a solvent, wherein C.I. I. The present invention relates to a green pigment dispersion for a color filter containing CI Pigment Green 59.

また、本発明は、(2)前記顔料分散剤が3級アミノ基及び/又は4級アンモニウム基を有し、3mgKOH/g以上のアミン価を有し、ブロック型構造であるアクリル系重合体を含む前記(1)項記載のカラーフィルター用緑色顔料分散物に関する。   Also, the present invention provides (2) an acrylic polymer having a block type structure, wherein the pigment dispersant has a tertiary amino group and / or a quaternary ammonium group, has an amine value of 3 mgKOH / g or more. The present invention relates to a green pigment dispersion for a color filter according to the above (1).

また、本発明は、(3)前記顔料がC.I.ピグメントイエロー185を含む前記(1)項または(2)項に記載のカラーフィルター用緑色顔料分散物に関する。   Further, the present invention provides (3) a method in which the pigment is C.I. I. The present invention relates to the green pigment dispersion for color filters according to the above (1) or (2), which contains CI Pigment Yellow 185.

また、本発明は、(4)前記緑色顔料と前記黄色顔料との質量比率が、95/5〜40/60である前記(1)項〜(3)項のいずれかに記載のカラーフィルター用緑色顔料分散物に関する。   The present invention also provides (4) the color filter according to any one of (1) to (3), wherein the mass ratio of the green pigment to the yellow pigment is 95/5 to 40/60. It relates to a green pigment dispersion.

また、本発明は、(5)前記顔料が微粒子化処理された顔料である前記(1)項〜(4)項のいずれかに記載のカラーフィルター用緑色顔料分散物に関する。   The present invention also relates to (5) the green pigment dispersion for a color filter according to any one of the above items (1) to (4), wherein the pigment is a pigment that has been subjected to fine particle treatment.

また、本発明は、(6)さらに、C.I.ピグメントイエロー185のスルホン化物を含む前記(1)項〜(5)項のいずれかに記載のカラーフィルター用緑色顔料分散物に関する。   The present invention also provides (6) a C.I. I. The present invention relates to the green pigment dispersion for a color filter according to any one of the above items (1) to (5), which contains a sulfonated product of CI Pigment Yellow 185.

また、本発明は、(7)前記(1)項〜(6)項に記載のカラーフィルター用緑色顔料分散物により形成された塗布層を有するカラーフィルターに関する。   The present invention also relates to (7) a color filter having a coating layer formed from the green pigment dispersion for a color filter according to any one of the above items (1) to (6).

なお、本発明においてアミン価とは、樹脂の固形分1gを中和するのに必要な塩酸量に対して当量となる水酸化カリウムの質量(mg)を表し、JIS K 7237に記載の方法に準ずる方法により測定される値である。   In the present invention, the amine value refers to the mass (mg) of potassium hydroxide which is equivalent to the amount of hydrochloric acid necessary to neutralize 1 g of the solid content of the resin, and according to the method described in JIS K 7237. This is a value measured by the method according to the following.

本発明においては、顔料として緑色顔料を用い、好ましくは黄色顔料を併用する。   In the present invention, a green pigment is used as the pigment, and a yellow pigment is preferably used in combination.

前記の緑色顔料としては、C.I.ピグメントグリーン59(カラーインデックス名)が必須成分として使用される。C.I.ピグメントグリーン59を使用することによって、得られたカラーフィルターの緑色着色組成物からなる層が薄く、明度が高く、かつバランスに優れた発色とすることができる。本発明における緑色顔料及び/又は黄色顔料としては、C.I.ピグメントグリーン59の光透過率を実質的に低下しない範囲において、他の緑色顔料も併用できる。
そして本発明のカラーフィルター用緑色着色組成物により得られた塗膜は、厚さが2.55μmにおいて、xが0.200〜0.240、好ましくは0.210〜0.230、さらに好ましくは0.215〜0.228であり、yが0.650〜0.705、好ましくは0.660〜0.690、さらに好ましくは0.665〜0.675、Yが37.0〜48.0、好ましくは38.0〜48.0である。
Examples of the green pigment include C.I. I. Pigment Green 59 (color index name) is used as an essential component. C. I. By using Pigment Green 59, the layer of the green color composition of the obtained color filter can be made thin, high in brightness, and excellent in color development. Examples of the green pigment and / or yellow pigment in the present invention include C.I. I. Other green pigments can be used in combination as long as the light transmittance of the pigment green 59 is not substantially reduced.
And the coating film obtained by the green coloring composition for a color filter of the present invention has a thickness of 2.55 μm, x of 0.200 to 0.240, preferably 0.210 to 0.230, more preferably 0.215 to 0.228, y is 0.650 to 0.705, preferably 0.660 to 0.690, more preferably 0.665 to 0.675, and Y is 37.0 to 48.0. , Preferably 38.0 to 48.0.

黄色顔料としては、C.I.ピグメントイエロー185(カラーインデックス名)等が使用される。中でもC.I.ピグメントイエロー185が本発明の目的を達成する上で好ましく、その他の黄色顔料としては、C.I.ピグメントイエロー185の光透過率を実質的に低下しない範囲において、他の黄色顔料を併用してもよい。   As the yellow pigment, C.I. I. Pigment Yellow 185 (color index name) or the like is used. Among them, C.I. I. Pigment Yellow 185 is preferred for achieving the object of the present invention, and other yellow pigments include C.I. I. Other yellow pigments may be used in combination as long as the light transmittance of Pigment Yellow 185 is not substantially reduced.

本発明において、緑色顔料と黄色顔料の配合割合は、重量比で緑色顔料/黄色顔料が95/5〜40/60とされることが好ましい。   In the present invention, the mixing ratio of the green pigment and the yellow pigment is preferably such that the weight ratio of the green pigment / the yellow pigment is 95/5 to 40/60.

本発明の顔料は、高い明度や高いコントラストを得るために微粒子化処理した顔料を使用することが好ましい。微粒子化処理を行うことにより、顔料の一次粒子径を更に微細にかつ均一にすることができる。
上記微粒子化処理としては、例えば、未処理着色顔料、水溶性の無機塩(塩化ナトリウム、塩化バリウム、塩化カリウム等で好ましくは塩化ナトリウムで、使用する水溶性の無機塩の平均粒子径としては50μm以下のものが好ましい)、及び、上記水溶性の無機塩を実質的に溶解しない水溶性分散媒体(アルコキシアルコール類、グリコール類、エーテル類等)を含む混合物を、ニーダー、ロールミル、ボールミル、アトライター、サンドミル、特開2006−192385号公報に記載のプラネタリーミキサーである井上製作所(株)社製のトリミックス(商標名)、連続式一軸混練機である浅田鉄工(株)社製のミラクルKCK等の混練装置で混練した後、上記水溶性の無機塩及び上記水溶性分散媒体を除去するソルトミリングを行い、微粒子化処理を行うことが好ましい。
As the pigment of the present invention, it is preferable to use a pigment which has been subjected to fine particle treatment in order to obtain high brightness and high contrast. By performing the micronization treatment, the primary particle diameter of the pigment can be made finer and more uniform.
Examples of the fine particle treatment include untreated color pigments, water-soluble inorganic salts (eg, sodium chloride such as sodium chloride, barium chloride, and potassium chloride, preferably sodium chloride). The water-soluble inorganic salt used has an average particle size of 50 μm. A mixture containing a water-soluble dispersion medium (alkoxy alcohols, glycols, ethers, etc.) that does not substantially dissolve the water-soluble inorganic salt is mixed with a kneader, a roll mill, a ball mill, an attritor. Trimix (trade name) manufactured by Inoue Seisakusho Co., Ltd., which is a planetary mixer described in JP-A-2006-192385, and Miracle KCK manufactured by Asada Tekko Co., Ltd., which is a continuous single-screw kneader. After kneading with a kneading device such as, and salt milling to remove the water-soluble inorganic salt and the water-soluble dispersion medium It is preferred to perform the atomization treatment.

本発明においては、C.I.ピグメントイエロー185のスルホン化物を併用する事が好ましい。具体的には、黄色顔料の微粒子化処理においてC.I.ピグメントイエロー185のスルホン化物を併用する方法や、単独で微粒子化処理された黄色顔料を分散する工程においてC.I.ピグメントイエロー185のスルホン化物を併用する方法などが挙げられる。
C.I.ピグメントイエロー185のスルホン化物の使用量は、黄色顔料100質量部に対して0.5〜30質量部、好ましくは3〜15質量部である。
In the present invention, C.I. I. Pigment Yellow 185 is preferably used in combination. More specifically, C.I. I. Pigment Yellow 185 in the combined use method or in the step of dispersing the finely divided yellow pigment alone. I. Pigment Yellow 185 and a combination thereof.
C. I. The amount of the sulfonated product of Pigment Yellow 185 is 0.5 to 30 parts by mass, preferably 3 to 15 parts by mass, per 100 parts by mass of the yellow pigment.

本発明に用いるカラーフィルター用緑色顔料分散物に使用する顔料分散剤としては、3級アミノ基及び/又は4級アンモニウム基を有し、3mgKOH/g以上のアミン価を有し、ブロック型構造であるアクリル系重合体が必須成分として使用される。
このような顔料分散剤としては、DISPERBYK−2001、DISPERBYK−2000、BYK−LPN6919、BYK−LPN21116、BYK−LPN22102(いずれもビックケミー社製)等が例示でき、これらは単独でまたは併用して使用できる。
The pigment dispersant used in the green pigment dispersion for a color filter used in the present invention has a tertiary amino group and / or a quaternary ammonium group, has an amine value of 3 mgKOH / g or more, and has a block structure. Certain acrylic polymers are used as essential components.
Examples of such a pigment dispersant include DISPERBYK-2001, DISPERBYK-2000, BYK-LPN6919, BYK-LPN21116, BYK-LPN22102 (all manufactured by BYK-Chemie), and these can be used alone or in combination. .

本発明の顔料組成物において、前記顔料分散剤の使用量は、顔料100質量部に対して1〜100質量部であることが好ましく、より好ましくは1〜60質量部である。前記顔料分散剤の含有量が1質量部より小さいと顔料分散効果が低下する場合があり、一方100質量部を超える場合は、現像性が低下する等のおそれがある。   In the pigment composition of the present invention, the amount of the pigment dispersant to be used is preferably 1 to 100 parts by mass, more preferably 1 to 60 parts by mass, per 100 parts by mass of the pigment. If the content of the pigment dispersant is less than 1 part by mass, the pigment dispersing effect may be reduced, while if it exceeds 100 parts by mass, the developability may be reduced.

また、前記顔料分散剤以外に、必要に応じ界面活性剤を併用することも可能である。このような界面活性剤としては、イオン性界面活性剤とノニオン性界面活性剤が挙げられ、イオン性界面活性剤としては、カチオン性界面活性剤、アニオン性界面活性剤および両性界面活性剤があげられる。カチオン性界面活性剤としては、脂肪族アミン類、第4級アンモニウム塩類、アルキルピリジウム塩類が例示できる。アニオン性界面活性剤としては、脂肪酸塩類、硫酸エステル類、スルホン酸塩類、リン酸エステル類等が例示できる。両性活性剤としては、アミノ酸塩類等が例示できる。ノニオン系界面活性剤としては、ポリオキシエチレンアルキルエーテル類、ポリオキシエチレンアルキルフェニルエーテル類、ポリオキシエチレンアルキルエステル類、ソルビタンアルキルエステル類、ポリオキシエチレンソルビタンアルキルエステル類等が例示できる。   In addition to the pigment dispersant, a surfactant may be used in combination as needed. Examples of such a surfactant include an ionic surfactant and a nonionic surfactant, and examples of the ionic surfactant include a cationic surfactant, an anionic surfactant and an amphoteric surfactant. Can be Examples of the cationic surfactant include aliphatic amines, quaternary ammonium salts, and alkylpyridium salts. Examples of the anionic surfactant include fatty acid salts, sulfates, sulfonates, phosphates, and the like. Examples of the amphoteric activator include amino acid salts and the like. Examples of the nonionic surfactant include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene alkyl esters, sorbitan alkyl esters, and polyoxyethylene sorbitan alkyl esters.

本発明に用いるカラーフィルター用緑色顔料分散物に使用する溶剤としては、顔料分散剤を溶解し、かつ、顔料を安定的に分散させることができる溶剤が好ましい。
このような溶剤の具体例としては、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、ジ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、プロピレングリコールモノエチルエーテル等の(ポリ)アルキレングリコールモノアルキルエーテル類、エチレングリコールモノメチルエーテルアセテート、エチ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モノエチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート等の(ポリ)アルキ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エチルエーテル、ジエチレングリコールメチルエチルエーテル、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、メチルイソブチルケトン、シクロヘキサノン、2−ヘプタノン、3−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、2−ヒドロキシプロピオン酸エチル等の乳酸アルキルエステル類、2−ヒドロキシ−2−メチルプロピオン酸エチル、3−メチル−3−メトキシブチルプロピオネート、3−メトキシプロピオン酸メチル、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メチル、3−エトキシプロピオン酸エチル、エトキシ酢酸エチル、ヒドロキシ酢酸エステル、酢酸エチル、酢酸n−ブチル、酢酸イソブチル、プロピオン酸n−ブチル、アセト酢酸メチル、ぎ酸n−アミル、ピルビン酸エチル等のエステル類、トルエン、キシレン等の芳香族炭化水素類、N−メチルピロリドン、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド等のアミド類を例示できる。これら溶剤は、単独で又は2種以上を混合して使用することができる。また、これら溶剤の使用量は、顔料分散物の全量に対して60〜80重量%の割合で使用することが好ましい。
As the solvent used for the green pigment dispersion for a color filter used in the present invention, a solvent that can dissolve the pigment dispersant and stably disperse the pigment is preferable.
Specific examples of such a solvent include (poly) alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether. , Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monoethyl ether acetate, (poly) alkylene glycol monoalkyl ether acetates such as propylene glycol monomethyl ether acetate, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, tet Ethers such as hydrofuran, ketones such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone and 3-heptanone; alkyl lactates such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate; Ethyl 2-methylpropionate, 3-methyl-3-methoxybutylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate , Hydroxyacetate, ethyl acetate, n-butyl acetate, isobutyl acetate, n-butyl propionate, methyl acetoacetate, n-amyl formate, ethyl pyruvate and the like, and aromatic hydrocarbons such as toluene and xylene N- methylpyrrolidone, N, N- dimethylformamide, N, amides such as N- dimethylacetamide can be exemplified. These solvents can be used alone or in combination of two or more. The amount of these solvents used is preferably 60 to 80% by weight based on the total amount of the pigment dispersion.

本発明のカラーフィルター用緑色顔料組成物は、緑色顔料、黄色顔料、顔料分散剤、溶剤等を混合し、超音波分散機、ビーズミル、3本ロール、ボールミル、サンドミル、ホモジナイザー、ニーダー等を用いて混練し分散処理することにより得られる。   The green pigment composition for a color filter of the present invention is obtained by mixing a green pigment, a yellow pigment, a pigment dispersant, a solvent, and the like, and using an ultrasonic disperser, a bead mill, a three-roll, a ball mill, a sand mill, a homogenizer, a kneader, and the like. It is obtained by kneading and dispersing.

前記の分散処理に際しては、顔料分散剤および/または溶剤は、その全量を分散処理時に顔料と共に用いてもよく、顔料分散剤の一部を分散処理後に加えてもよい。   In the above-described dispersion treatment, the entire amount of the pigment dispersant and / or the solvent may be used together with the pigment during the dispersion treatment, or a part of the pigment dispersant may be added after the dispersion treatment.

本発明のカラーフィルター用緑色顔料分散物は、通常、バインダー樹脂、光重合性不飽和結合を分子内に1個以上有する光重合性化合物および光重合開始剤、必要に応じ溶剤、その他の添加剤と混合して顔料分散レジスト組成物として、カラーフィルターの形成に使用される。その際の各種配合剤、調製法などは従来のものがとくに制限されず、使用できる。   The green pigment dispersion for a color filter of the present invention is generally a binder resin, a photopolymerizable compound having at least one photopolymerizable unsaturated bond in a molecule, a photopolymerization initiator, a solvent, if necessary, and other additives. And used as a pigment-dispersed resist composition to form a color filter. At this time, the conventional compounding agents, preparation methods and the like can be used without particular limitation.

以下、実施例を挙げて本発明をより具体的に説明するが、本発明はこれら実施例に限定されるものではない。なお、特に断りのない限り、本実施例において「部」および「%」は「重量部」および「重量%」を表わす。
<顔料>
D1155(C.I.ピグメントイエロー185、商品名Paliotol Yellow D1155、BASF社製)
6268EC(C.I.ピグメントイエロー150、商品名クロモファインイエロー6268EC、大日精化社製)
L0960HD(C.I.ピグメントイエロー138、商品名PaliotolYellow L0960HD、BASF社製)
Green S(C.I.ピグメントグリーン7、商品名ファーストゲングリーン S、DIC社製)
A110(C.I.ピグメントグリーン58、商品名ファーストゲングリーンA110、DIC社製)
C100(C.I.ピグメントグリーン59、商品名ファーストゲングリーンC100、DIC社製)
<顔料分散剤>
BYK−LPN21116(3級アミノ基及び4級アンモニウム基を有し、約29mgKOH/gのアミン価を有し、ブロック型構造であるアクリル系重合体、固形分40%、ビックケミー社製)
<バインダー樹脂>
BnMA/MAA共重合体(ベンジルメタクリレート/メタクリル酸共重合体、理論酸価120mgKOH/g、質量平均分子量25,000)
<溶剤>
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)
<光重合性化合物>
DPHA(ジペンタエリスリトールヘキサアクリレート)
<光重合開始剤>
Ir369(2−ベンジル−(ジメチルアミノ)−1−(4−モルフォリノフェニル)−1−ブタノン、商品名イルガキュア369、BASF社製)
Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples. In the examples, “parts” and “%” represent “parts by weight” and “% by weight” unless otherwise specified.
<Pigment>
D1155 (CI Pigment Yellow 185, trade name Pariotol Yellow D1155, manufactured by BASF)
6268EC (CI Pigment Yellow 150, trade name Chromofine Yellow 6268EC, manufactured by Dainichi Seika)
L0960HD (CI Pigment Yellow 138, trade name Palitolol Yellow L0960HD, manufactured by BASF)
Green S (CI Pigment Green 7, trade name First Gen Green S, manufactured by DIC)
A110 (CI Pigment Green 58, trade name First Gen Green A110, manufactured by DIC)
C100 (CI Pigment Green 59, trade name First Gen Green C100, manufactured by DIC)
<Pigment dispersant>
BYK-LPN21116 (acrylic polymer having a tertiary amino group and a quaternary ammonium group, an amine value of about 29 mgKOH / g, and a block structure, solid content 40%, manufactured by BYK-Chemie)
<Binder resin>
BnMA / MAA copolymer (benzyl methacrylate / methacrylic acid copolymer, theoretical acid value 120 mgKOH / g, mass average molecular weight 25,000)
<Solvent>
PGMEA (propylene glycol monomethyl ether acetate)
<Photopolymerizable compound>
DPHA (dipentaerythritol hexaacrylate)
<Photopolymerization initiator>
Ir369 (2-benzyl- (dimethylamino) -1- (4-morpholinophenyl) -1-butanone, trade name Irgacure 369, manufactured by BASF)

(D1155スルホン化物)
100ml三角フラスコに濃硫酸を30ml仕込み、マグネチックスターラーで撹拌しながらD1155を10g投入し、室温で30分撹拌した。1Lビーカーに水50gと氷50gの混合物を入れ、上記反応物をこの氷水中に注ぎ、マグネチックスターラーで30分撹拌した。これを減圧下で濾過・水洗し、得られた固体を乾燥させてD1155スルホン化物を12g得た。
(微粒子化D1155)
ニーダー(商品名:KHD−2、井上製作所製)のタンクに、D1155を100質量部、粒径20μmの塩化ナトリウム1000質量部、ジエチレングリコール240質量部を投入し、75℃で10時間混練しソルトミリングを行った。次に得られた混練物1300質量部を3リットルの温水に投入し、70℃に加熱しながら1時間撹拌しスラリー状とした。ろ過、水洗を繰り返し塩化ナトリウム及びジエチレングリコールを除いた後、40℃にて乾燥し、95質量部の微粒子化D1155を得た。
(微粒子化D1155(スルホン化物含有))
ニーダー(商品名:KHD−2、井上製作所製)のタンクに、D1155を100質量部、粒径20μmの塩化ナトリウム1000質量部、D1155スルホン化物7質量部、ジエチレングリコール240質量部を投入し、75℃で10時間混練しソルトミリングを行った。次に得られた混練物1300質量部を3リットルの温水に投入し、70℃に加熱しながら1時間撹拌しスラリー状とした。ろ過、水洗を繰り返し塩化ナトリウム及びジエチレングリコールを除いた後、40℃にて乾燥し、98質量部の微粒子化D1155(スルホン化物含有)を得た。
(D1155 sulfonate)
30 ml of concentrated sulfuric acid was charged into a 100 ml Erlenmeyer flask, and 10 g of D1155 was added thereto while stirring with a magnetic stirrer, followed by stirring at room temperature for 30 minutes. A mixture of 50 g of water and 50 g of ice was placed in a 1 L beaker, and the reaction product was poured into the ice water and stirred with a magnetic stirrer for 30 minutes. This was filtered and washed with water under reduced pressure, and the obtained solid was dried to obtain 12 g of sulfonated D1155.
(Particulate D1155)
100 parts by mass of D1155, 1000 parts by mass of sodium chloride having a particle diameter of 20 μm, and 240 parts by mass of diethylene glycol are put into a tank of a kneader (trade name: KHD-2, manufactured by Inoue Seisakusho), and the mixture is kneaded at 75 ° C. for 10 hours and salt milled. Was done. Next, 1300 parts by mass of the obtained kneaded material was poured into 3 liters of warm water, and stirred for 1 hour while heating to 70 ° C. to form a slurry. Filtration and washing were repeated to remove sodium chloride and diethylene glycol, followed by drying at 40 ° C. to obtain 95 parts by mass of micronized D1155.
(Particulate D1155 (containing sulfonated product))
100 parts by mass of D1155, 1000 parts by mass of sodium chloride having a particle size of 20 μm, 7 parts by mass of a sulfonated D1155, and 240 parts by mass of diethylene glycol were charged into a tank of a kneader (trade name: KHD-2, manufactured by Inoue Seisakusho) at 75 ° C. For 10 hours to perform salt milling. Next, 1300 parts by mass of the obtained kneaded material was poured into 3 liters of warm water, and stirred for 1 hour while heating to 70 ° C. to form a slurry. Filtration and washing were repeated to remove sodium chloride and diethylene glycol, followed by drying at 40 ° C to obtain 98 parts by mass of microparticulated D1155 (containing a sulfonated product).

<カラーフィルター用顔料分散組成物>
上記微粒子化顔料、又は微粒子化していない各種顔料、顔料分散剤、D1155スルホン化物、バインダー樹脂(BnMA/MAA共重合体)、有機溶剤(PGMEA)を表1の組成となるように混合し、0.2mmΦのジルコニアビーズを用いてペイントコンディショナーで6時間混練し、カラーフィルター用顔料分散組成物1〜8を得た。
<Pigment dispersion composition for color filter>
The above-mentioned finely divided pigment or various non-finely divided pigments, a pigment dispersant, a sulfonated D1155, a binder resin (BnMA / MAA copolymer), and an organic solvent (PGMEA) were mixed so that the composition shown in Table 1 was obtained. The mixture was kneaded with zirconia beads having a diameter of 0.2 mm by a paint conditioner for 6 hours to obtain pigment dispersion compositions 1 to 8 for color filters.

Figure 0006645859
Figure 0006645859

<カラーフィルター用顔料分散レジスト組成物>
次いで、カラーフィルター用顔料分散組成物1〜8と、BnMA/MAA共重合体、DPHA、Ir369、PGMEAを、表2の組成になるように高速撹拌機を用いて均一に混合した後、孔径3μmのメンブランフィルターでろ過し、カラーフィルター用顔料分散レジスト組成物1〜8を得た。
<Pigment-dispersed resist composition for color filter>
Next, the pigment dispersion compositions 1 to 8 for a color filter, the BnMA / MAA copolymer, DPHA, Ir369, and PGMEA were uniformly mixed using a high-speed stirrer so that the compositions shown in Table 2 were obtained. To obtain pigment-dispersed resist compositions 1 to 8 for color filters.

Figure 0006645859
Figure 0006645859

<実施例1〜2及び比較例1〜10のカラーフィルター用緑色顔料分散レジスト組成物>
表3の顔料割合となるようにカラーフィルター用顔料分散レジスト組成物1〜8から選択された組成物を均一混合し、実施例1〜2及び比較例1〜10のカラーフィルター用緑色顔料分散レジスト組成物を得た。
<Green pigment-dispersed resist compositions for color filters of Examples 1 and 2 and Comparative Examples 1 to 10>
Compositions selected from the pigment-dispersed resist compositions for color filters 1 to 8 were uniformly mixed so that the pigment ratios shown in Table 3 were obtained, and the green pigment-dispersed resists for color filters of Examples 1 and 2 and Comparative Examples 1 to 10 were mixed. A composition was obtained.

Figure 0006645859
Figure 0006645859

(評価)
<カラーフィルター用緑色顔料分散レジスト組成物の色特性の評価>
実施例1〜2及び比較例1〜10のカラーフィルター用緑色顔料分散レジスト組成物を、スピンコーターを用いてガラス基板上に塗布した。次いで、100℃で3分間プレベークした後、高圧水銀灯で露光し、更に230℃で30分間ポストベークした。次いで、実施例1〜2及び比較例1〜10の各レジストの色特性(x,y,Y)を分光光度計(島津製作所社製、UV−2500PC、C光源2°視野)で測定した。実施例1〜2及び比較例1〜10では、色度x=0.224、y=0.669での膜厚、明度Yを求めた。
(Evaluation)
<Evaluation of color characteristics of green pigment-dispersed resist composition for color filter>
The green pigment-dispersed resist compositions for color filters of Examples 1 and 2 and Comparative Examples 1 to 10 were applied on a glass substrate using a spin coater. Next, after pre-baking at 100 ° C. for 3 minutes, exposure was performed with a high-pressure mercury lamp, and post-baking was further performed at 230 ° C. for 30 minutes. Next, the color characteristics (x, y, Y) of each of the resists of Examples 1 and 2 and Comparative Examples 1 to 10 were measured with a spectrophotometer (manufactured by Shimadzu Corporation, UV-2500PC, C light source 2 ° visual field). In Examples 1 and 2 and Comparative Examples 1 to 10, the film thickness and lightness Y at chromaticity x = 0.224 and y = 0.669 were determined.

本発明に沿った例である実施例1〜2によれば、カラーフィルター用緑色顔料レジスト組成物は、Yの値が高く、かつ膜厚が小さいのでカラーフィルターとして適切な光学的性質を備えることが解る。
一方、C.I.ピグメントグリーン59を使用せずに、ほかの顔料を採用してなる比較例1〜10によれば、xとyの値が実施例と共通しても、Yの値が低いために、カラーフィルター用として適切に使用することができない。
According to Examples 1-2, which are examples in accordance with the present invention, the green pigment resist composition for a color filter has a high Y value and a small film thickness, so that it has appropriate optical properties as a color filter. I understand.
On the other hand, C.I. I. According to Comparative Examples 1 to 10 in which other pigments were employed without using Pigment Green 59, even though the values of x and y were the same as those of the example, the value of Y was low. Can not be used properly.

表3からわかるように、緑色顔料としてC.I.ピグメントグリーン59を使用したカラーフィルター用緑色顔料分散物は、小さい膜厚においても明度が非常に高いことがわかる。 As can be seen from Table 3, C.I. I. It can be seen that the green pigment dispersion for a color filter using Pigment Green 59 has extremely high brightness even at a small film thickness.

Claims (5)

顔料、顔料分散剤、C.I.ピグメントイエロー185のスルホン化物および溶剤を含み、顔料としてC.I.ピグメントグリーン59と黄色顔料を含み、C.I.ピグメントグリーン59と該黄色顔料との質量比率が、95/5〜40/60であるカラーフィルター用緑色顔料分散物。 Pigments, pigment dispersants , C.I. I. Pigment Yellow 185 and a solvent. I. Pigment Green 59 and a yellow pigment. I. A green pigment dispersion for a color filter , wherein the mass ratio between Pigment Green 59 and the yellow pigment is 95/5 to 40/60 . 前記顔料分散剤が3級アミノ基及び/又は4級アンモニウム基を有し、3mgKOH/g以上のアミン価を有し、ブロック型構造であるアクリル系重合体を含む請求項1記載のカラーフィルター用緑色顔料分散物。   2. The color filter according to claim 1, wherein the pigment dispersant has a tertiary amino group and / or a quaternary ammonium group, has an amine value of 3 mgKOH / g or more, and contains an acrylic polymer having a block structure. 3. Green pigment dispersion. 前記黄色顔料がC.I.ピグメントイエロー185を含む請求項1または2に記載のカラーフィルター用緑色顔料分散物。 The yellow pigment is C.I. I. The green pigment dispersion for a color filter according to claim 1, comprising Pigment Yellow 185. 前記顔料が微粒子化処理された顔料である請求項1〜のいずれかに記載のカラーフィルター用緑色顔料分散物。 The green pigment dispersion for a color filter according to any one of claims 1 to 3 , wherein the pigment is a pigment that has been subjected to fine particle treatment. 請求項1〜4のいずれかに記載のカラーフィルター用緑色顔料分散物により形成された塗布層を有するカラーフィルター。 A color filter having a coating layer formed by the color filter for a green pigment dispersion according to any one of claims 1-4.
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