TW200821362A - Pigment dispersion composition, photocurable composition, color filter, and method for producing the color filter - Google Patents

Pigment dispersion composition, photocurable composition, color filter, and method for producing the color filter Download PDF

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TW200821362A
TW200821362A TW096132172A TW96132172A TW200821362A TW 200821362 A TW200821362 A TW 200821362A TW 096132172 A TW096132172 A TW 096132172A TW 96132172 A TW96132172 A TW 96132172A TW 200821362 A TW200821362 A TW 200821362A
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pigment
acid
group
compound
polymer
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TW096132172A
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Chinese (zh)
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TWI417355B (en
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Shigetomo Tsujihata
Koichi Sugihara
Hidenori Takahashi
Kazuhiro Fujimaki
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Fujifilm Corp
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    • 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
    • G03F7/0045Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • 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
    • G03F7/0047Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • 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
    • G03F7/20Exposure; Apparatus therefor

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Ceramic Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

The present invention provides a pigment dispersion composition and photocurable composition having excellent pigment dispersibility and dispersion stability, color filter providing high contrast, and method for producing such a color filter. The invention provides a pigment dispersion composition, including, in an organic solvent, a pigment and a polymer having a monomer represented by the following general formula (1): wherein R1 represents a hydrogen atom or a substituted or non-substituted alkyl group; R2 represents an alkylene group; W represents -C(=O)O-, -CONH-, a phenylene group or the like; X represents -S-, -CONH-, -C(=O)S-, -NHCONH-, -NHC(=O)S- or the like; Y represents -NR3-, -O-, -S- or -N= and forms a cyclic structure by linking these groups with an N atom via an adjacent atom group; R3 represents a hydrogen atom, alkyl group or aryl group; and m and n each independently represent 0 or 1.

Description

200821362 九、發明說明: 【發明所屬之技術領域】 本發明係有關於一種顏料分散組成物、含有其之光硬化 性組成物、使用該光硬化性組成物而成之彩色濾光片及該 彩色濾光片之製造方法。 【先前技術】 光硬化性組成物係含有已使有機顏料或無機顏料分散 的顏料分散組成物、多官能單體、光聚合引發劑、鹼可溶 性樹脂及其他的成分。彩色濾光片能夠藉由使用光硬化性 組成物並使用光微影法等形成著色圖案來製造。 近年來,彩色濾光片作爲液晶顯示元件(LCD)用途,不 只是監視器亦有往電視(TV)用途擴大的傾向。隨著該用途 擴大的傾向,在色度、對比等亦要求高度的顏色特性。又, 在影像感測器(固體攝像元件)用途亦同樣地要求高度的顏 色特性。 針對於如上述的要求,要求以更微細的狀態來使顏料 分散(良好的分散性)、及以安定狀態來使其分散(良好的分 散安定性)。顏料分散性不充分時,所形成的著色光阻膜會 產生毛邊(fringe)(邊緣部的鋸齒紋)或表面凹凸,會有所製 造的彩色濾光片的色度或尺寸精確度低落、或對比明顯地 變差之問題。又,顏料的分散安定性不充分時,在彩色濾 光片的製造步驟,特別是,在光硬化性組成物的塗布步驟 容易產生膜厚度均勻性降低、在曝光步驟容易產生感光敏 感度降低、在顯影步驟之鹼溶解性降低等問題。而且,顏 200821362 料的分散安定性差時,隨著時間的經過,亦會有光硬化性 組成物的構成成分產生凝聚而使黏度上升、使適用期變爲 極短之問題。 但是,使顏料的粒徑微細化時,因爲顏料粒子的表面 積變大,顏料粒子間的凝聚力變大,欲兼具高水準的分散 性及分散安定性,多半係困難的。 爲了解決如此的問題,已開發各式各樣的顏料分散 劑。此等分散劑之中,含有巨大單體(在末端具有乙烯性不 飽和基之低聚物)之共聚物係有用的。有揭示藉由使用含該 巨大單體(在末端具有乙烯性不飽和基之低聚物)之共聚物 來進行分散處理,能夠得到顏料粒徑小、分散安定性優良 之顏料分散液(例如,參照專利文獻1、2)。 但是,因爲含有專利文獻1、2所記載的巨大單體之共 聚物未具有促進對顏料吸附之官能基,單獨時沒有作爲分 散劑之功能,會有必須與其他分散劑倂用之問題。又,使 φ 用含有此種巨大單體之共聚物作爲顏料的分散劑時,雖然 能夠抑制在局分子分散劑所見到的增黏作用,但是因爲顏 料的微細化未充分進行,會有顏料的分散性不充分之問題。 爲了提升顏料的分散安定性,有揭示具有有機色料的 部分結構(例如’參照專利文獻3)、含氮雜環(例如,參照 專利文獻4)、具有環狀醯亞胺基(例如,參照專利文獻5) 之接枝聚合物。 但是’顏料的分散性及分散安定性優良的顏料分散組 200821362 成物、及含有其之光硬化性組成物,目前尙未能提供。 [專利文獻1]特開平8-25 9 876號公報 [專利文獻2]特開平1 0-339949號公報 [專利文獻3]特開2003 -26950號公報 [專利文獻4]特開2003-26949號公報 [專利文獻5]特開2003 -27 7 67 3號公報 【發明內容】 [發明所欲解決之課題] 鑒於前述先前技術的問題點,本發明係以達成以下目 的爲課題。 亦即,本發明的目的係提供一種顏料分散性及分散安 定性優良之顏料分散組成物,並且因爲顏料分散性及分散 安定性優良,藉由曝光硬化能夠提供一種能夠形成光透射 性及對比優良的被膜之光硬化性組成物。 本發明的其他目的係提供一種能夠得到高對比之彩色 濾光片、及此種彩色濾光片之製造方法。 [解決課題之手段] 本發明者等專心硏討之結果,發現藉由使用具有特定結構 之聚合物作爲顏料分散劑,能夠解決上述課題,而完成了 本發明。 亦即,爲了解決前述課題之手段如下。 < 1 >一種顏料分散組成物,係在有機溶劑中含有顏料、 及含有來自下述通式(1)所示單體之共聚合單位的聚合物。 200821362 [化學式1] 通式(1)200821362 IX. OBJECTS OF THE INVENTION: The present invention relates to a pigment dispersion composition, a photocurable composition containing the same, a color filter using the photocurable composition, and the color A method of manufacturing a filter. [Prior Art] The photocurable composition contains a pigment dispersion composition in which an organic pigment or an inorganic pigment has been dispersed, a polyfunctional monomer, a photopolymerization initiator, an alkali-soluble resin, and other components. The color filter can be produced by forming a colored pattern using a photocurable composition and using a photolithography method or the like. In recent years, color filters have been used as liquid crystal display elements (LCDs), and there is a tendency that the use of televisions (TVs) is not limited to monitors. As the use tends to expand, high color characteristics are also required in chromaticity, contrast, and the like. Also, the use of image sensors (solid-state imaging devices) requires a high degree of color characteristics. In response to the above requirements, it is required to disperse the pigment in a finer state (good dispersibility) and to disperse it in a stable state (good dispersion stability). When the pigment dispersibility is insufficient, the formed colored photoresist film may have a fringe (a zigzag pattern at the edge portion) or a surface unevenness, and the color filter or the dimensional accuracy of the manufactured color filter may be lowered, or The contrast is significantly worse. In addition, when the dispersion stability of the pigment is insufficient, in the step of producing the color filter, in particular, the film thickness uniformity is likely to be lowered in the coating step of the photocurable composition, and the photosensitive sensitivity is likely to be lowered in the exposure step. Problems such as a decrease in alkali solubility in the development step. In addition, when the dispersion stability of the material of the film 200821362 is poor, the composition of the photocurable composition is agglomerated and the viscosity is increased, and the application period is extremely short. However, when the particle size of the pigment is made fine, the surface area of the pigment particles is increased, and the cohesive force between the pigment particles is increased, and it is difficult to achieve high level of dispersibility and dispersion stability. In order to solve such problems, various pigment dispersants have been developed. Among these dispersants, copolymers containing a large monomer (an oligomer having an ethylenically unsaturated group at the terminal) are useful. It is disclosed that by using a copolymer containing the macromonomer (an oligomer having an ethylenically unsaturated group at the terminal), a pigment dispersion having a small pigment particle size and excellent dispersion stability can be obtained (for example, Refer to Patent Documents 1, 2). However, since the copolymer containing the macromonomers described in Patent Documents 1 and 2 does not have a functional group for promoting adsorption of the pigment, it does not function as a dispersing agent alone, and it is necessary to use it with other dispersing agents. Further, when φ is used as a dispersing agent for a pigment containing a copolymer of such a large monomer, the viscosity-increasing effect seen in the local molecular dispersant can be suppressed, but the pigment is not sufficiently refined, and there is a pigment. The problem of insufficient dispersion. In order to improve the dispersion stability of the pigment, a partial structure having an organic coloring material (for example, 'Reference Patent Document 3), a nitrogen-containing hetero ring (for example, refer to Patent Document 4), and a cyclic quinone imine group (for example, reference) are disclosed. Patent Document 5) A graft polymer. However, the pigment dispersion group in which the dispersibility and dispersion stability of the pigment are excellent, and the photocurable composition containing the same are not provided at present. [Patent Document 1] JP-A-2003-26950 [Patent Document 3] JP-A-2003-26950 [Patent Document 4] JP-A-2003-26949 [Problem to be Solved by the Invention] In view of the problems of the prior art described above, the present invention has been made in order to achieve the following object. That is, the object of the present invention is to provide a pigment dispersion composition excellent in pigment dispersibility and dispersion stability, and because of excellent pigment dispersibility and dispersion stability, it is possible to provide light transmittance and contrast by exposure hardening. The photocurable composition of the film. Another object of the present invention is to provide a color filter capable of obtaining high contrast and a method of manufacturing such a color filter. [Means for Solving the Problem] The inventors of the present invention have found that the above problems can be solved by using a polymer having a specific structure as a pigment dispersant, and the present invention has been completed. That is, the means for solving the above problems are as follows. < 1 > A pigment dispersion composition comprising a pigment in an organic solvent and a polymer containing a copolymerization unit derived from a monomer represented by the following formula (1). 200821362 [Chemical Formula 1] General Formula (1)

在通式(1),R1表示氫原子、或是取代或未取代之;院基° R2 表示伸烷基。W 表示- CO-、-C( = 0)〇、-C0NH-、-0C( = 0)、 或伸苯基。X 表示- 0-、-S-、-c( = 〇)0-、-C〇NH-、-C( = 〇)s·、 Φ -NHCONH-、-NHC(:〇)0-、-NHC( = 0)S-、-〇c( = 0)·、-〇CONH_、 或- NHC〇-。Y表示-NR3-、-0-、-S-、或**N=,透過與其鄰接 的原子團與N原子連結而形成環狀結構° R3表示氫原子、 烷基或芳基。m及η各自獨立地表示〇或1° &lt; 2 &gt;如&lt; 1 &gt;之顏料分散組成物,其中在前述通式(1),Υ 透過鄰接的原子團與Ν原子連結而形成環狀結構係縮合環 結構。 ^ &lt;3&gt;如&lt;1&gt;或&lt;2&gt;之顏料分散組成物,其中前述聚合物係 更含有來自在末端具有乙烯性不飽和鍵之聚合性低聚物的 共聚合單位之接枝共聚物。 &lt;4&gt;如&lt;1&gt;或&lt;2&gt;之顏料分散組成物,其中前述聚合物係 更含有來自具有酸基之單體的共聚合單位之聚合物。 &lt;5&gt;如&lt;1&gt;之顏料分散組成物,其中前述聚合物的酸價 係10〜150毫克ΚΟΗ/克。 &lt;6&gt;如&lt;1&gt;之顏料分散組成物,其中前述顏料係選自由 C.I.顏料黃139、C.I·顏料黃150、C.I·顏料綠36、C.I·顏料 200821362 紅177、C.I·顏料紅254、C.I.顏料藍15 : 6、及C.I·顏料紫 23所組成群組中之至少1種顏料。 &lt;7&gt;—種光硬化性組成物,係含有前述&lt;1&gt;之顏料分散 組成物、光聚合性化合物、及光聚合引發劑。 &lt;8〉如&lt;7&gt;之光硬化性組成物,其中更含有鹼可溶性橫f 脂。 &lt;9&gt;如&lt;7&gt;或&lt;8&gt;之光硬化性組成物,其中前述光聚合引 發劑係選自由三阱系化合物、咯吩二聚物類系化合物、及 肟系化合物所組成群組中之至少1種光聚合引發劑。 &lt;1〇&gt;如&lt;7&gt;或&lt;8&gt;之光硬化性組成物,係彩色濾光片用。 &lt;11&gt; 一種彩色濾光片,具有在基板上使用如&lt;10&gt;之光 硬化性組成物而構成之著色圖案。 &lt; 1 2&gt;—種彩色濾光片之製法,係包含感光性膜形成步 驟及著色圖案形成步驟,該感光性膜形成步驟係將前述 &lt; 10&gt;之光硬化性組成物直接或透過其他的層賦予在基板上 來形成感光性膜;而該著色圖案形成步驟係在所形成的感 光性膜上依次進行圖案曝光及顯影來形成著色圖案。 [發明之效果] 依照本發明,能夠提供一種具有高顏料分散性及分散安 定性之顏料分散組成物,並且因爲顏料分散性及分散安定 性優良,藉由曝光硬化能夠提供一種能夠形成光透射性及 對比優良的被膜之光硬化性組成物。 又,依照本發明,能夠提供一種能夠得到高對比之彩色 -10- 200821362 濾光片、及此種彩色濾光片之製法。 【實施方式】 以下,詳細地說明本發明的顏料分散組成物、光硬化性 組成物、彩色濾光片及其製法。 &lt;顏料分散組成物&gt; 本發明的顏料分散組成物係在有機溶劑中含有顏料、及 含有由來自下述通式(1)所示單體之共聚合單位的聚合物。 [含有來自通式(1)所示單體之共聚合單位的聚合物] 本發明的顏料分散組成物係須含有含來自下述通式U) 所示單體之共聚合單位的聚合物。 在本發明的顏料分散組成物,聚合物係能夠發揮作爲顏 料分散劑的功能之物。在以下說明,會有將「含有來自通 式(1)所示單體之共聚合單位的聚合物」簡稱爲「特定顏料 分散劑」而說明之情形。 Γ [化學式2] 通式(1)In the formula (1), R1 represents a hydrogen atom, or is substituted or unsubstituted; and the substituent R ° represents an alkylene group. W represents -CO-, -C( = 0)〇, -C0NH-, -0C( = 0), or phenyl. X represents - 0-, -S-, -c( = 〇)0-, -C〇NH-, -C( = 〇)s·, Φ -NHCONH-, -NHC(:〇)0-, -NHC ( = 0) S-, -〇c( = 0)·, -〇CONH_, or - NHC〇-. Y represents -NR3-, -0-, -S-, or **N=, and a cyclic structure is formed by linking an atomic group adjacent thereto to an N atom. R3 represents a hydrogen atom, an alkyl group or an aryl group. m and η each independently represent a pigment dispersion composition of 〇 or 1° &lt; 2 &gt;&lt; 1 &gt;, wherein, in the above formula (1), Υ is bonded to a ruthenium atom by a contiguous atomic group to form a ring Structure is a condensed ring structure. [3] The pigment dispersion composition of <1> or <2>, wherein the polymer system further contains a graft unit derived from a copolymerization unit having a polymerizable oligomer having an ethylenically unsaturated bond at a terminal. Copolymer. &lt;4&gt; The pigment dispersion composition of &lt;1&gt; or &lt;2&gt;, wherein the polymer further contains a polymer derived from a copolymerization unit of a monomer having an acid group. &lt;5&gt; The pigment dispersion composition of &lt;1&gt;, wherein the acid value of the polymer is 10 to 150 mg Å/g. &lt;6&gt; The pigment dispersion composition of &lt;1&gt;, wherein the pigment is selected from the group consisting of CI Pigment Yellow 139, CI Pigment Yellow 150, CI Pigment Green 36, CI Pigment 200821362 Red 177, CI Pigment Red 254 At least one of the group consisting of CI Pigment Blue 15:6 and CI·Pigment Violet 23 is at least one pigment. &lt;7&gt; The photocurable composition contains the pigment dispersion composition of the above &lt;1&gt;, a photopolymerizable compound, and a photopolymerization initiator. &lt;8&gt; The photocurable composition of &lt;7&gt;, further comprising an alkali-soluble horizontal fat. &lt;9&gt; The photocurable composition of <7> or <8>, wherein the photopolymerization initiator is selected from the group consisting of a tritrap compound, a spheroid dimer compound, and a lanthanoid compound. At least one photopolymerization initiator in the group. &lt;1〇&gt; The photocurable composition of &lt;7&gt; or &lt;8&gt; is used for a color filter. &lt;11&gt; A color filter having a colored pattern formed by using a photocurable composition such as &lt;10&gt; on a substrate. &lt; 1 2&gt; The method for producing a color filter comprising a photosensitive film forming step and a coloring pattern forming step of directly or transmitting the photocurable composition of the above &lt;10&gt; The layer is formed on the substrate to form a photosensitive film; and the colored pattern forming step sequentially performs pattern exposure and development on the formed photosensitive film to form a colored pattern. [Effects of the Invention] According to the present invention, it is possible to provide a pigment dispersion composition having high pigment dispersibility and dispersion stability, and because of excellent pigment dispersibility and dispersion stability, it is possible to provide light transmittance by exposure hardening. And a photocurable composition of an excellent film. Further, according to the present invention, it is possible to provide a color -10-200821362 filter which can obtain high contrast, and a method of manufacturing such a color filter. [Embodiment] Hereinafter, the pigment dispersion composition, the photocurable composition, the color filter, and the method for producing the same according to the present invention will be described in detail. &lt;Pigment Dispersion Composition&gt; The pigment dispersion composition of the present invention contains a pigment in an organic solvent and a polymer containing a copolymerization unit derived from a monomer represented by the following formula (1). [Polymer containing a copolymerization unit derived from a monomer represented by the general formula (1)] The pigment dispersion composition of the present invention is required to contain a polymer containing a copolymerization unit derived from a monomer represented by the following formula U). In the pigment dispersion composition of the present invention, the polymer system can function as a pigment dispersant. In the following description, a case where "a polymer containing a copolymerization unit derived from a monomer represented by the general formula (1)" is simply referred to as a "specific pigment dispersant" will be described. Γ [Chemical Formula 2] General Formula (1)

在通式(1 ),R1係表示氫原子或取代或未取代之烷基。 R2係表示伸烷基。W係表示-CO-、-C( = 0)0-、-CONH-、 -〇C( = 〇)-、或伸苯基。X係表示-〇-、-S-、-C( = 〇)0-、-CONH-、In the formula (1), R1 represents a hydrogen atom or a substituted or unsubstituted alkyl group. R2 represents an alkylene group. The W system represents -CO-, -C(=0)0-, -CONH-, -〇C(=〇)-, or a phenyl group. The X system indicates -〇-, -S-, -C( = 〇)0-, -CONH-,

-QCONH-、或-NHC〇-。Y 係表示-NR3-、 -〇-、 -S-、或-N=, 200821362 :¾過與其鄰接的原子團與N原子連結而形成環狀結構。R3 係表示氫原子、烷基或芳基。㈤及n係各自獨立地表示〇 或1。 以下’對在本發明的重要成分之特定顏料分散劑中所必 須的共聚合單位,通式(1)所示單體詳細地進行說明。 在通式(1)’ R 1係表示氫原子、或取代或未取代的烷基。 R 1所不之烷基以碳數1〜1 2的烷基爲較佳,以碳數1〜8 φ 的烷基爲更佳’以碳數1〜4的烷基爲特佳。 R1所示之烷基係取代烷基爾,能夠導入的取代基可舉 出例如經基、院氧基、芳氧基、醯氧基、及鹵素基等。 R1所示之較佳的烷基,具體上可舉出甲基、乙基、正 丙基、異丙基、正丁基、異丁基、第三丁基、正己基、環 己基、2-羥基乙基、3-羥基丙基、2-羥基丙基、2-甲氧基乙 基等。 R1以氫原子或碳數1〜4之烷基爲特佳。 # R2係表示伸烷基。 R2所示之伸烷基,以碳數1〜1 2之伸烷基爲較佳,以碳 數1〜8之伸烷基爲更佳,以碳數1〜4之伸烷基爲特佳。 R2所示之伸烷基若能夠導入時亦可具有取代基’該取 代基可舉出例如羥基、烷氧基、芳氧基、醯氧基等。 R2所示之較佳伸院基,具體上可舉出亞甲基、伸乙基、 伸丙基、三亞甲基、四亞甲基等。 W 係表示- C〇-、-C( = 0)〇-、-CONH-、-〇C( = 0)-、或伸苯 -12- 200821362 基,以-C( = 0)0-、-CONH-、或伸苯基爲佳。 Y係表示N R3 -、- 0 _、- S -、或_ N = ’透過與其鄰接的原 子團與N原子連結而形成環狀結構。 R3係表示氫原子、烷基、或芳基。R3所示之烷基可適 合舉出碳數1〜12的烷基,R3所示之芳基’可適合舉出苯基、 萘基等。 R3以氫原子、或碳數1〜4之烷基爲更佳’以氫原子、 或是甲基爲特佳。 Y以-3-、-1^-、或_]^ =爲特佳。 Y透過與其鄰接的原子團與N原子連結而形_成環狀結 構,可舉出例如咪唑環、嘧啶環、三唑環、四唑環、噻唑 環、唑環等單環結構;及苯并咪唑環、苯并噻唑環、苯 并曙唑環、嘌呤環、喹唑環、咂啶環等縮合環結構,從顏 料的親和性觀點而言,以縮合環結構爲佳。縮合環結構之 中,可舉出苯并咪唑環、苯并噻唑環、及苯并噚唑環爲特 佳。 X 係表示-0-、-S-、-C( = 〇)0-、-C0NH-、-C( = 〇)S-、 -NHCONH-、_NHC( = 〇)0_、_NHC( = 〇)S-、-〇C( = 〇)_、_〇C〇NH_、 或 _NHC〇_。X 以 _〇_、_S_、-C〇NH-、_NHC0NH_、及·ΝΗ(:( = 〇)3_ 爲特佳。 m及η係各自獨立地表示0或1,m及η以都是1爲特 佳。 以下,舉出在通式(1)所示之單體之較佳具體例(單體 Μ-1〜單體〜Μ-18),但是本發明未限定於此等。 -13- 200821362 [化學式3] \ M Q ΡΗ3 ΜΗ Η Η b〇r^NYNYN) Ο Ν-ΝΗ Μ- 3-QCONH-, or -NHC〇-. The Y system represents -NR3-, -〇-, -S-, or -N=, 200821362: 3⁄4, and the adjacent atomic group is bonded to the N atom to form a cyclic structure. R3 represents a hydrogen atom, an alkyl group or an aryl group. (5) and n are independent representations of 〇 or 1. Hereinafter, the monomer represented by the formula (1) will be described in detail in the copolymerization unit necessary for the specific pigment dispersant of the important component of the present invention. In the formula (1)', R 1 represents a hydrogen atom or a substituted or unsubstituted alkyl group. The alkyl group which is not represented by R 1 is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 φ carbon atoms, and particularly preferably an alkyl group having 1 to 4 carbon atoms. The alkyl group represented by R1 is a substituted alkyl group, and examples of the substituent which can be introduced include a thiol group, an anthraceneoxy group, an aryloxy group, a decyloxy group, and a halogen group. Preferred alkyl groups represented by R1 include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, cyclohexyl, and 2- Hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl, 2-methoxyethyl, and the like. R1 is particularly preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. # R2 represents an alkylene group. The alkylene group represented by R2 is preferably an alkylene group having 1 to 12 carbon atoms, more preferably an alkylene group having 1 to 8 carbon atoms, and particularly preferably an alkylene group having 1 to 4 carbon atoms. . The alkylene group represented by R2 may have a substituent when it can be introduced. The substituent group may, for example, be a hydroxyl group, an alkoxy group, an aryloxy group or a decyloxy group. The preferred stretching base represented by R2 may specifically be a methylene group, an ethylidene group, a propyl group, a trimethylene group or a tetramethylene group. The W system represents - C〇-, -C( = 0)〇-, -CONH-, -〇C( = 0)-, or benzo-12-200821362 base, with -C( = 0)0-,- CONH-, or phenyl is preferred. The Y system indicates that N R3 -, - 0 _, - S -, or _ N = ' is connected to the adjacent atom and N atom to form a cyclic structure. R3 represents a hydrogen atom, an alkyl group, or an aryl group. The alkyl group represented by R3 is preferably an alkyl group having 1 to 12 carbon atoms, and the aryl group represented by R3 is preferably a phenyl group or a naphthyl group. R3 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and is particularly preferably a hydrogen atom or a methyl group. Y is particularly preferred as -3-, -1^-, or _]^. Y is formed into a cyclic structure by being bonded to an adjacent atomic group and an N atom, and examples thereof include a monocyclic structure such as an imidazole ring, a pyrimidine ring, a triazole ring, a tetrazole ring, a thiazole ring, and an azole ring; and benzimidazole. The condensed ring structure such as a ring, a benzothiazole ring, a benzoxazole ring, an anthracene ring, a quinazoline ring or an acridine ring is preferably a condensed ring structure from the viewpoint of affinity of the pigment. Among the condensed ring structures, a benzimidazole ring, a benzothiazole ring, and a benzoxazole ring are particularly preferred. X series means -0-, -S-, -C( = 〇)0-, -C0NH-, -C( = 〇)S-, -NHCONH-, _NHC( = 〇)0_, _NHC( = 〇)S -, -〇C( = 〇)_, _〇C〇NH_, or _NHC〇_. X is particularly preferably _〇_, _S_, -C〇NH-, _NHC0NH_, and ·ΝΗ(:( = 〇)3_. m and η are each independently represented as 0 or 1, and m and η are both 1 In the following, preferred examples of the monomer represented by the formula (1) (monomer Μ-1 to monomer Μ-18) are exemplified, but the present invention is not limited thereto. 200821362 [Chemical Formula 3] \ MQ ΡΗ3 ΜΗ Η Η b〇r^NYNYN) Ο Ν-ΝΗ Μ- 3

Η Η ηΗ Η η

Η Η Η^Μ C〇f^Η Η Η^Μ C〇f^

200821362 [化學式4]200821362 [Chemical Formula 4]

1SH71SH7

IH8 從賦予顏料的分散安定性之觀點,本發明之特定顏料分 散劑以含有來自前述通式(1)所示單體之共聚合單位、且同 時更含有來自末端具有乙烯性不飽和鍵的聚合性低聚物之 共聚合單位的接枝共聚物爲特佳。 此種末端具有乙烯性不飽和鍵的聚合性低聚物因爲係 具有規定分子量所以亦稱爲巨大單體。在以下的說明,會 有將本發明之「末端具有乙烯性不飽和鍵的聚合性低聚物-簡稱爲「聚合性低聚物」、或「巨大單體」之情形。 -15- 200821362 在本發明,依照需要所使用的聚合性低聚物係由聚合物 鏈部分、及其末端具有乙烯性不飽和雙鍵之能夠聚合的官 能基部分所構成。從能夠得到需要的接枝聚合之觀點,此 種具有乙烯性不飽和雙鍵之基以只有在聚合物鏈之一側的 末端具有爲佳。具有乙烯性不飽和雙鍵之基,以(甲基)丙 烯醯基.、乙烯基爲佳,以(甲基)丙烯醯基爲特佳。 又,該巨大單體以換算聚苯乙烯之數量平均分子量(Μη) 爲1000〜10000的範圍爲較佳,以2000〜9000的範圍爲特佳。 通常,上述聚合物鏈的部分係選自由(甲基)丙烯酸院 酯、苯乙烯及其衍生物、丙烯腈、乙酸乙烯酯及丁二烯所 組成群組中之至少一種單體所形成的單獨聚合物或共聚 物、或是聚環氧乙烷、聚環氧丙烷、聚己內酯。 上述聚合性低聚物以下述通式(2)所示之低聚物爲佳。 [化學式5] 通式(2) 癱 V Ρ11 ?13IH8 The specific pigment dispersant of the present invention contains a copolymerization unit derived from the monomer represented by the above formula (1) and further contains an ethylenically unsaturated bond derived from the terminal, from the viewpoint of imparting dispersion stability to the pigment. The graft copolymer of the copolymerized unit of the oligomer is particularly preferred. The polymerizable oligomer having an ethylenically unsaturated bond at the terminal is also called a macromonomer because it has a predetermined molecular weight. In the following description, the polymerizable oligomer having an ethylenically unsaturated bond at the terminal of the present invention may be simply referred to as "polymerizable oligomer" or "large monomer". In the present invention, the polymerizable oligomer used as required is composed of a polymer chain moiety and a polymerizable functional group moiety having an ethylenically unsaturated double bond at its terminal. From the viewpoint of obtaining a desired graft polymerization, such a group having an ethylenically unsaturated double bond is preferably present only at one end of the polymer chain. The group having an ethylenically unsaturated double bond is preferably a (meth) acrylonitrile group or a vinyl group, and particularly preferably a (meth) acrylonitrile group. Further, the macromonomer is preferably in the range of from 1,000 to 10,000 in terms of the number average molecular weight (??) of the converted polystyrene, and particularly preferably in the range of from 2,000 to 9000. Typically, the portion of the above polymer chain is selected from the group consisting of at least one monomer selected from the group consisting of (meth)acrylic acid esters, styrene and its derivatives, acrylonitrile, vinyl acetate, and butadiene. Polymer or copolymer, or polyethylene oxide, polypropylene oxide, polycaprolactone. The polymerizable oligomer is preferably an oligomer represented by the following formula (2). [Chemical Formula 5] General Formula (2) 瘫 V Ρ11 ?13

響 - R12-S-fcH2-G^H h 〇 T r 通式(2)中,R11及R13係各自獨立地表示氫原子或甲基。 R12係表示含有碳原子數1〜12的伸烷基之連結基,該連 結基亦可以是碳原子數1〜1 2之伸烷基,亦可以是複數個該 伸烷基透過酯鍵、醚鍵、醯胺鍵等連結而成之物。較佳之 R12係碳原子數1〜4的伸烷基、或是碳數1〜4的伸烷基透過 酯鍵連結之基。R12所示之伸烷基亦可以更具有取代基(例 -16 - 200821362 如羥基)。 Y係表示未具有取代基之苯基、具有1個碳原子數1〜4 的烷基之苯基或-COOR14。在此’ R14係表示碳原子數1~6 的烷基、苯基或碳原子數7〜10的芳烷基。γ以苯基或 -COOR14爲佳,在此,其中R14係表示碳原子數1〜12的烷基。 q係表示20〜200之整數。 在本發明,能夠使用於合成特定顏料分散劑之聚合性低 聚物(巨大單體)之較佳例子,可舉出聚(甲基)丙烯酸甲酯、 ^ 聚(甲基)丙烯酸正丁酯及聚(甲基)丙烯酸異丁酯、及在聚苯 乙嫌的一個分子末端鍵結(甲基)丙燒醯基的聚合物。市場 可取得之此種聚合性低聚物可舉出一末端甲基丙烯醯化之 聚苯乙烯低聚物(Mn = 6000、商品名·· AS-6、東亞合成化學 工業(股)製)、一末端甲基丙烯醯化之聚甲基丙烯酸甲酯低 聚物(Mn = 6000、商品名:AA-6、東亞合成化學工業(股)製)、 及一末端甲基丙烯醯化之聚甲基丙烯酸正丁酯低聚物 φ (Μη = 6〇00、商品名:AB-6、東亞合成化學工業(股)製)。 本發明之特定顏料分散劑以更含有來自具有酸基的單 體之共聚合單位爲佳。因爲特定顏料分散劑更含有來自具 有酸基的單體之共聚合單位,例如應用於使用光微影法將 本發明的顏料分散組成物形成圖案時,能夠更提升圖案成 形性。 具有酸基之單體可舉出丙烯酸、甲基丙烯酸、巴豆酸、 α -氯丙烯酸、桂皮酸等的不飽和單羧酸類;順丁烯二酸、 -17- 200821362 順丁烯二酸酐、反丁烯二酸、伊康酸、伊康酸酐、檸康酸、 檸康酸酐、中康酸等不飽和二羧酸或其酐類;3價以上的 不飽和多元羧酸或其酐類;琥珀酸單(2-丙烯醯氧基乙基) 酯、琥珀酸單(2-甲基丙烯醯氧基乙基)酯、酞酸單(2_丙烯 醯氧基乙基)酯、酞酸單(2·甲基丙烯醯東基乙基)酯等2價 以上的多元羧酸的單[(甲基)丙烯醯氧基烷基]酯類;ω -羧 基-聚己內酯一丙烯酸酯、羧基·聚己內酯一甲基丙嫌酸 酯等兩末端羧基聚合物的一(甲基)丙烯酸酯類等。 本發明之特定顏料分散劑在不損害其效果的範圍內,亦 可更含有能夠共聚合的乙燃型單體作爲共聚合成分。 在此,能夠使用乙烯型單體沒有特別限制,例如,以(甲 基)丙烯酸酯類、巴豆酸酯類、乙烯基酯類、順丁烯二酸二 酯類、反丁烯二酸二酯類、伊康酸二酯類、(甲基)丙烯醯 胺類、乙烯基醚類、乙烯醇的酯類、苯乙烯類、(甲基)丙 烯腈等爲佳。如此的乙烯型單體的具體例,可舉出例如以 φ 下的化合物。 (甲基)丙烯酸酯類的例子可舉出(甲基)丙烯酸甲酯、(甲 基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸異丙 酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸異丁酯、(甲基)丙 烯酸第三丁酯、(甲基)丙烯酸正己酯、(甲基)丙烯酸環己 酯、(甲基)丙烯酸第三丁基環己酯、(甲基)丙烯酸2-乙基己 酯、(甲基)丙烯酸第三辛酯、(甲基)丙烯酸十二烷酯、(甲 基)丙烯酸十八烷酯、(甲基)丙烯酸乙醯氧基乙酯、(甲基) -18- 200821362 甲 2 二2-( 酸酸 烯烯 丙 丙 ¾)¾) E甲 /1\ 、 酯酯 乙乙 基基 羥氧 二乙 酸 2 烯酸 丙烯 基丙 \—/ (¥基 T甲 匕日 ( 酉 、 苯酯 酸乙 烯基 丙氧 甲氧基.乙氧基)乙酯、(甲基)丙烯酸3-苯氧基-2-羥基丙酯、 (甲基)丙烯酸苄酯、(甲基)丙烯酸二甘醇一甲基醚、(甲基) 丙烯酸二甘醇一乙基醚、(甲基)丙烯酸三甘醇一甲基醚、(甲 基)丙烯酸三甘醇一乙基醚、(甲基)丙烯酸聚乙二醇一甲基 醚、(甲基)丙烯酸聚乙二醇一乙基醚、(甲基)丙烯酸々-苯 氧基乙氧基乙酯、(甲基)丙烯酸壬基苯氧基聚乙二醇、(甲 基)丙烯酸二環戊烯酯、(甲基)丙烯酸二環戊烯氧基乙酯、 (甲基)丙烯酸三氟乙酯、(甲基)丙烯酸八氟戊酯、(甲基)丙 烯酸全氟辛基乙酯、(甲基)丙烯酸二環戊酯、(甲基)丙烯酸 三溴苯酯、(甲基)丙烯酸三溴苯氧基乙酯等。 又,在本說明書,表示「丙烯基、甲基丙烯基」之任一 者或雙方時,會有記載爲「(甲基)丙烯基」之情形。 巴豆酸酯類的例子可舉出巴豆酸丁酯、及巴豆酸己酯 • 等。 乙烯基酯類的例子可舉出乙酸乙烯酯、丙酸乙烯酯、丁 酸乙烯酯、甲氧基乙酸乙烯酯、及苯甲酸乙烯酯等。 順丁烯二酸二酯類的例子可舉出順丁烯二酸二甲酯、順 丁烯二酸二乙酯、及順丁烯二酸二丁酯等。 反丁烯二酸二酯類類的例子可舉出反丁烯二酸二甲 酯、反丁烯二酸二乙酯、及反丁烯二酸二丁酯等。伊康酸 二酯類類的例子可舉出伊康酸二甲酯、伊康酸二乙酯、及 -19- 200821362 伊康酸二丁酯等。 (甲基)丙烯醯胺類的例子可舉出(甲基)丙烯醯胺、N-甲 基(甲基)丙烯醯胺、N-乙基(甲基)丙烯醯胺、N-丙基(甲基) 丙烯醯胺、N-異丙基(甲基)丙烯醯胺、N-正丁基(甲基)丙烯 醯胺、N-第三丁基(甲基)丙烯醯胺、N-環己基(甲基)丙烯醯 胺、N-(2-甲氧基乙基)(甲基)丙烯醯胺、N,N-二甲基(甲基) 丙烯醯胺、N,N-二乙基(甲基)丙烯醯胺、N-苯基(甲基)丙烯 醯胺、N-苄基(甲基)丙烯醯胺、(甲基)丙烯醯味啉、二丙酮 丙烯醯胺等。 苯乙烯類的例子可舉出苯乙烯、甲基苯乙烯、二甲基苯 乙烯、三甲基苯乙烯、乙基苯乙烯、異丙基苯乙烯、丁基 苯乙烯、羥基苯乙烯、甲氧基苯乙烯、丁氧基苯乙烯、乙 醯氧基苯乙烯、氯苯乙烯、二氯苯乙烯、溴苯乙烯、氯甲 基苯乙烯、被能夠用酸性物質脫除保護的基(例如 t-Boc(t-butyl〇Xycarbonyl ;第三丁氧羰基)等)保護之羥基苯 乙烯、乙烯基苯甲酸甲酯、及α -甲基苯乙烯等。、 乙烯基醚類的例子可舉出甲基乙烯基醚、丁基乙烯基 醚、己基乙烯基醚、及甲氧基乙基乙烯基醚等。 本發明之特定顏料分散劑之酸價以10〜150毫克Κ0Η/ 克爲較佳,以20〜140毫克Κ0Η/克爲更佳,以30〜120毫克 Κ0Η/克爲特佳。 特定顏料分散劑的酸價在10〜150毫克Κ0Η/克的範圍 時’將本發明的顏料分散組成物應用作爲光阻液時,在適 -20- 200821362 當地維持光阻液的鹼溶解性、達成良好的顯影性之同時, 達成優良的顏料分散安定性。 將特定顏料分散劑的酸價維持在上述適當範圍之手 段’可舉出例如使構成特定顏料分散劑之聚合物含有1 %以 上具有酸基的共聚合成分之手段,或是使構成特定顏料分 散劑之聚合物藉由高分子反應,來附加例如酸酐之手段。 在此,特定顏料分散劑的酸價係指,中和i克該顏料分 • 散劑所必要的氫氧化鉀的毫克數。酸價的單位係毫克KOH/ 克 I價係封樹肖曰溶液進fr滴定驗溶液(例如,氯氧化納水 溶液或氫氧化鉀水溶液)來求取中和點,能夠從到達中和點 爲止所需要的鹼溶液的量算出。在滴定時,例如藉由使用 酣酞等滴定指示劑之滴定法或藉由使用自動電位差滴定裝 置之方法,來求取中和點。 本發明之特定顏料分散劑的較佳態樣,可適合舉出含有 2〜50質量%來自前述通式(1)所示單體之共聚合單位、且更 # 含有10〜90質量%來自在末端具有乙烯性不飽和鍵的聚合 性低聚物之共聚合單位、idO質量%來自具有酸基的單體 之共聚合單位、及〇〜20質量%來自乙烯型單體之共聚合單 位之共聚物。 本發明之特定顏料分散劑的較佳分子量,係重量平均分 子量(Mw)以15000〜200000爲佳,數量平均分子量(Mn)以 8000〜100000爲佳。又,分子量能夠藉由gpc測定。 以下’將能夠適合使用於本發明的顏料分散組成物之特 -21- 200821362 定顏料分散劑的具體例[例示化合物1〜例示化合物16]與其 重量平均分子量一同舉出,但是本發明未限定於此等。 例示化合物(1):前述單體M-2/末端甲基丙烯醯化聚甲 基丙烯酸甲酯共聚物(10/90質量%、重量平均分子量爲 50000、酸價:0毫克KOH/克) 例示化合物(2):前述單體M-2/甲基丙烯酸/末端甲基丙 烯醯化聚甲基丙烯酸甲酯共聚物(10/15/75質量%、重量平 均分子量爲30000、酸價:98毫克KOH/克) ^ 例示化合物(3):前述單體M-3/甲基丙烯酸2-羥基乙酯/ 末端甲基丙烯醯化聚甲基丙烯酸甲酯共聚物(5/10/85質量 %、重量平均分子量爲40000、酸價:0毫克KOH/克) 例示化合物(4):前述單體M-3/甲基丙烯酸/甲基丙烯酸 苄酯共聚物/末端甲基丙烯醯化聚甲基丙烯酸甲酯共聚物 (15/5/10/65質量%、重量平均分子量爲60000、酸價:33毫 克KOH/克) φ 例示化合物(5):前述單體M-4/末端甲基丙烯醯化聚甲 基丙烯酸甲酯共聚物(10/90質量%、重量平均分子量爲 80000、酸價:0毫克KOH/克) 例示化合物(6):前述單體M-4/甲基丙烯酸/末端甲基丙 烯醯化聚甲基丙烯酸甲酯共聚物(1 0/1 5 /7 5質量%、重量平 均分子量爲30000、酸價:98毫克KOH7克) 例示化合物(7):前述單體M-5/丙烯酸/末端甲基丙烯醯 化聚甲基丙烯酸甲酯共聚物(25/1 5/60質量%、重量平均分 -22- 200821362 子量爲60000、酸價:117毫克KOH/克) 例示化合物(8):前述單體M-5/末端甲基丙烯醯化聚甲 基丙烯酸丁酯共聚物(15/85質量%、重量平均分子羹爲 40000、酸價:〇毫克KOH/克) 例示化合物(9):前述單體M-6/甲基丙烯酸2-羥基乙酯/ 末端甲基丙烯醯化聚甲基丙烯酸甲酯共聚物(15/1 0/7 5質量 %、重量平均分子量爲80000、酸價:0毫克KOH/克) 例示化合物(10):前述單體M-6/末端甲基丙烯醯化聚甲 ^ 基丙烯酸甲酯共聚物(12/88質量%、重量平均分子量爲 50000、酸價:〇毫克KOH/克) 例示化合物(11):前述單體M-7/甲基丙烯酸/末端甲基 丙烯醯化聚甲基丙烯酸甲酯共聚物(10/15/75質量%、重量 平均分子量爲25000、酸價:98毫克KOH/克) 例示化合物(12):前述單體M-7/甲基丙烯酸/甲基丙烯 酸苄酯/甲氧基聚乙二醇甲基丙烯酸酯共聚物(10/10/5 0/3 0 φ 質量%、重量平均分子量爲40000、酸價:65毫克KOH/克) 例示化合物(13):前述單體M-10/甲基丙烯酸2-羥基乙 酯/末端甲基丙烯醯化聚苯乙烯共聚物(5/10/85質量%、重 量平均分子量爲20000、酸價:〇毫克KOH/克) 例示化合物(14):前述單體M-10/甲基丙烯酸/末端甲基 丙烯醯化聚甲基丙烯酸甲酯共聚物(10/15/75質量%、重量 平均分子量爲35000、酸價:98毫克KOH/克) 例示化合物(15):前述單體M-10/甲氧基聚乙二醇甲基 -23- 200821362 丙烯酸酯共聚物(15/85質量%、重量平均分子量爲15000、 酸價:0毫克KOH/克) 例示化合物(16):前述單體M-13/甲基丙烯酸/末端甲基 丙烯醯化聚甲基丙烯酸甲酯共聚物(1 〇/1 5 /7 5質量%、重量 平均分子量爲20000、酸價:98毫克KOH/克) 例示化合物(17):前述單體M-4/甲基丙烯酸/末端甲基 丙烯醯化聚甲基丙烯酸甲酯共聚物(10/15/75質量%、重量 平均分子量爲25000、酸價:98毫克KOH/克) 例示化合物(18):前述單體M-4/丙烯酸/末端甲基丙烯 醯化聚苯乙烯共聚物(10/10/80質量%、重量平均分子量爲 20000、酸價:78毫克KOH/克) 例示化合物(19):前述單體M-4/甲基丙嫌酸2-羥基乙酯 的琥珀酸酐加成物/末端甲基丙烯醯化聚甲基丙烯酸甲酯 共聚物(8/15/77質量%、重量平均分子量爲25000、酸價: 37毫克KOH/克) 例示化合物(20):前述單體M-4/丙烯酸/甲基丙烯酸苄 酯/末端甲基丙烯醯化聚甲基丙烯酸甲酯共聚物 (10/10/10/70質量%、重量平均分子量爲25000、酸價:78 毫克KOH/克) 例示化合物(21) ··前述單體M-10/丙烯酸/末端甲基丙烯 醯化聚甲基丙烯酸甲酯共聚物(1 5 /1 0/7 5質量%、重量平均 分子量爲25000、酸價:78毫克KOH/克) 例示化合物(22):前述單體M-11/甲基丙烯酸/末端甲基 -24 - 200821362 丙Μ醯化聚甲基丙烯酸甲酯共聚物(15/1〇/75質量%、重量 平均分子量爲25000、酸價:65毫克ΚΟΗ/克) 例示化合物(23):前述單體Μ-11/末端甲基丙烯醯化聚 甲基丙嫌酸甲酯共聚物(15/85質量%、重量平均分子量爲 30000、酸價:〇毫克ΚΟΗ/克) 在本發明’特定顏料分散劑之如上述的共聚物,能夠藉 由使前述通式(1)所示之單體、依照需要倂用的聚合性低聚 0 物或其他的單體,在溶劑中進行自由基聚合而得到。自由 基聚合引發劑能夠使用眾所周知的化合物,適合使用偶氮 引發劑(例如,二甲基-2,2’ -偶氮雙(丙酸2-甲酯)、偶氮雙 ζ 異丁腈、2,2’ -偶氮雙(2-甲脒基丙烷)2鹽酸鹽等)、過氧化 物(過氧化苯甲醯、過硫酸鉀等)。亦可添加引發劑且更添 加鏈轉移劑(例如2 -氫硫基乙醇、3 ·氫硫基丙酸、2 -氫硫基 乙酸、十二烷基硫醇)而合成。 又,後述具體的合成例。 • 相對於後述之顏料的質量,在顏料分散組成物中之特定 顏料分散劑的含量以0.5〜1 00質量%爲較佳,以3〜7 0質量% 爲更佳。顏料分散劑的量在此範圍內時,能夠得到充分的 顏料分散效果。又,即便添加顏料分散劑比1 00質量%多, 亦無法期待更提升顏料分散效果。 本發明的顏料分散組成物係在有機溶劑中含有顏料、及 特定顏料分散劑而成之物,亦能夠按照必要使用樹脂成分 等其他成分而構成。 -25- 200821362 因爲該顏料分散組成物係含有特定顏料分散劑,所以在 有機溶劑中之顏料的分散狀態變爲良好,能夠得到良好的 顏色特性’同時例如構成彩色濾光片時能夠得到高對比。 特別是在有機顏料中能夠發揮優良的分散效果。 [顏料] 本發明的顏料分散組成物係含有顏料,該顏料能夠適當 地選擇先前眾所周知的各種無機顏料或有機顏料而使用。 顏料不管是無機顏料或是有機顏料,考慮高透射率爲佳 時’以使用粒子尺寸盡量小之物爲佳。若亦考慮處理性時, 顏料的平均粒徑以〇·〇1微米〜0.1微米爲較佳,以0.01微米 〜0.05微米爲更佳。 前述無機顏料可舉出金屬氧化物、金屬錯合物等金屬化 合物。具體上可舉出鐵 '鈷、鋁、鎘、鉛、銅、鈦 '鎂、 鉻、鋅、銻等金屬氧化物、及前述金屬的複合氧化物等。 前述有機顏料可舉出例如以下之物。 C.I·顏料黃 11、24、31、53、83、93、99、108、109、 110、138、139、147、150、15卜 154、155 ^ 167、180、185、 199 ; C.I.顏料橙 36、38、43、71 ; C.I.顏料紅 81、1〇5、122、149、150、155、171、175、 176、 177、 209、 220、 224、 242、 254、 255、 264、 270; C.I.顏料紫 19、23、32、37、39 ; C · I ·顏料藍 1、2、1 5、1 5 ·· 1、1 5 ·· 3、1 5 : 6、1 6、2 2、 -26 - 200821362 60 ^ 66 ; C.I.顏料綠 7、36、37; C.I.顏料棕 25、28 ; C.I.顏料黑1、7 ; 本發明之顏料沒有特別限定,以下述顏料爲更佳 C.I.顏料黃 11、24、108、109、110、138、139、 151 、 154 、 167 、 180 、 185 ; C.I.顏料橙 36、71 ; • C.I·藏料紅 122、150、17 1、4 75、177、209、22 4, 254 、 255 、 264 ; C . I.顏料紫 1 9、2 3、3 7 ; C.I.顏料藍 15 : 1、15 : 3、15 : 6、16、22、60、 C.I.顏料綠36 C . I.顏料黑7 此等之中,以下述顏料爲特佳。 • C.I.顏料黃 139、150 C · I.顏料紅 1 7 7、2 5 4 C.I.顏料紫23 C.I.顏料藍15 : 6 C.I.顏料綠36 此等有機顏料能夠單獨使用、或是爲了提升色純 各種組合的方式使用。將組合的具體例列示於τ。 例如,紅色顏料能夠單獨使用蒽醌系顏料、菲系 150、 242、 66 ; 度而以 顏料、 -27- 200821362 二酮吡咯并吡咯系顏料,或是使用此等之至少一種與雙偶 氮系黃色顏料、異吲哚啉系黃色顏料、喹啉黃系黃色顏料 或與茈系紅色顏料之混合等。例如,蒽醌系顏料可舉出C. I. 顏料紅1 7 7,茈系顏料可舉出C . I.顏料紅1 5 5、C . I.顏料紅 2 24、二酮吡咯并吡咯系顏料可舉出C.I.顏料紅254,從色 再現性而言,以與C.I.顏料黃139混合爲佳。又,紅色顏 料與黃色顏料之質量比以100 : 5〜1 00 : 50爲佳。小於1〇〇 : 5時,難以抑制在400奈米〜500奈米的光透射率,會有無 法提高色純度之情形。又,大於100 : 5 0時,會有主波長 偏靠短波長,而大幅度偏離N T S C標準色相之情形。特別 是前述質量比以100 : 10〜1 00 : 30的範圍爲最佳。又,紅 色顏料彼此間之組合時,能夠合倂色度而調整。 又,綠色顏料能夠單獨使用鹵化酞青系顏料,又,亦能 夠使用其與雙偶氮系黃色顏料、喹啉黃系黃色顏料、甲亞 胺系黃色顏料或是異吲哚啉系黃色顏料之混合。例如,此 種例子以與C.I·顏料綠7、36、37與C.I.顏料黃83、C.I. 顏料黃138、C.I.顏料黃139、C.I_顏料黃150、C.I.顏料黃 180或C.I.顏料黃185混合爲佳。綠色顏料與黃色顏料的質 量比以1 0 0 : 5〜1 〇 〇 : 1 5 0爲佳。質量比小於1 0 Q : 5時,難 以抑制400奈米〜450奈米的光透射率,會有色純度無法提 升的情形。又,大於1 00 : 1 50時,主波長偏靠長波長,會 有大幅度偏離NTSC標準色相之情形。質量比以在1 〇〇 : 30〜100· 120的範圍爲特佳。 -28- 200821362 藍色顏料能夠單獨使用酞青系顏料、或是使用其與二曙 阱系紫色顏料之混合。例如,以C.I.顏料藍15 : 6與C.I· 顏料紫23之混合爲較佳。藍色顏料與紫色顏料之質量比以 100: 0〜100: 50爲較佳,以100: 5〜100: 30爲更佳。 又,黑色矩陣用顏料可舉出碳、鈦黑、氧化鐵、氧化鈦 之單獨或此等的混合,碳與鈦黑的組合爲佳。又,碳與鈦 黑的質重比以在1 0 0 : 〇〜1 Q 〇 : 6 0的範圍爲佳。大於1 0 0 : 6 0時,會有分散安定性低落之情形。 在顏料分散組成物中之顏料的含量,相對於該組成物的 總固體成分(質量),以40〜90質量%爲較佳,以50〜8〇質量 %爲更佳。顏料的含量在前述範圍內時,因色濃度充足而有 效確保優良的顏色特性。 [有機溶劑] 調製本發明的顏料分散組成物所使用的有機溶劑可舉 出2 -乙醯氧基-1-曱氧基丙院、1-甲氧基-2-丙醇、乙二醇一 φ 甲基醚、二甘醇一甲基醚、乙酸乙酯、乙酸丁酯、乳酸乙 酯、丙酮、甲基乙基酮、甲基異丁基酮、環己酮、正丙醇、 2-丙醇、正丁醇、環己醇、乙二醇、二甘醇、甲苯、二甲 苯等。 又’有機溶劑的添加量能夠按照顏料分散組成物的用途 等而適當地選擇。但是,使用於調製後述之光硬化性組成 物時,k處理性而g,能夠以含有顏料及顏料分散劑之固 體成分濃度爲5〜5〇質量%的方式添加。 -29- 200821362 調製本發明的顏料分散組成物,沒有特別限制,例如能 夠使用縱式或橫式的砂硏磨機、針盤式碾磨機、狹縫碾磨 機、超音波分散機等,藉由0.0 1〜1毫米粒徑的玻璃、氧化 锆等所製成的珠粒,將顏料、顏料分散劑、及溶劑進行微 分散處理而得到。 又,在進行珠粒分散之前,亦能夠使用二輥、三輥、球 磨機、轉筒篩碾磨機、分散機、捏合機、混練擠壓機、均 0 化器、摻合器、及單軸或雙軸擠壓機等,一邊賦予強剪切 力一邊進行混練分散處理。 又,關於混練、分散之詳細,在T.c. Patton著“塗料 流動及顔料分散 (Paint flow and Pigment Dispersion)” (1964 年 John Wiley and Sons 公司刊物)等有 記載。 本發明的顏料分散組成物除了形成彩色濾光片用以 外,亦能夠應用於噴墨用印墨等。 馨又,本發明之顏料分散組成物係彩色濾光片形成用途 時,以在鹼水溶液中可溶爲佳。 &lt;光硬化性組成物&gt; 本發明的光硬化性組成物係含有前述之本發明的顏料 分散組成物、光聚合物化合物、及光聚合引發劑,以更含 有鹼可溶性樹脂爲佳,亦能夠按照必要而含有其他成分。 因爲該光硬化性組成物含有前述本發明之特定顏料分 散劑,所以在組成物中顏料能夠保持良好的分散狀態、能 -30- 200821362 夠得到良好的顏色特性,且例如構成彩色濾光片時能夠同 時得到高對比。 以下,詳述在本發明的光硬化性組成物所含有的各成 分。 [顏料分散組成物] 本發明的光硬化性組成物係使用前述本發明的顏料分 散組成物之至少一種而構成。關於構成光硬化性組成物之 0 本發明的顏料分散組成物之詳細,係如前述。 在本發明的光硬化性組成物中之顏料分散組成物的含 量,相對於光硬化性組成物的總固體成分(質量),以顏料 的含量在5〜70質量%的範圍之量爲較佳,以在15〜60質量 %的範圍之量爲更佳。顏料分散組成物的含量在此範圍內 時,色濃度充足而有效確保優良的顏色特性。 [鹼可溶性樹脂] 本發明的光硬化性組成物以含有至少一種鹼可溶性樹 φ 脂爲佳,光硬化性組成物藉由含有鹼可溶性樹脂,在應用 於使用光微影法將該光硬化性組成物形成圖案時,能夠提 升圖案成形性。 鹼可溶性樹脂係線狀有機高分子聚合物,能夠從在分子 (較佳是鹼系共聚物、苯乙烯系共聚物爲主鏈之分子)中具 有至少1個促進鹼可溶性的基(例如羧基、磷酸基、磺酸基 等)之鹼可溶性樹脂中適當地選擇。其中,以在有機溶劑中 可溶、且能夠藉由弱鹼水溶液顯影之鹼可溶性樹脂爲更佳。 -31 - 200821362 製造鹼可溶性樹脂例如能夠應用藉由眾所周知的聚合 法之方法。藉由自由基聚合法製造鹼可溶性樹脂時之溫 度、壓力、自由基引發劑的種類及其量、溶劑的種類等等 之聚合條件,係該業者能夠容易地設定,亦能夠以實驗性 規定條件的方式來進行。 上述的線狀有機高分子聚合物以在側鏈具有羧酸之聚 合物爲佳。可舉出例如特開昭59-446 1 5號、特公昭54-34327 號、特公昭 5 8- 1 2577號、特公昭 54-25957號、特開昭 ^ 5 9-5 3 8 36號、特開昭5 9-7 1 048號的各公報所記載之甲基丙 烯酸共聚物、丙烯酸共聚物、伊康酸共聚物、巴豆酸共聚 物、順丁烯二酸共聚物、部分酯化順丁烯二酸共聚物等, 以及在側鏈具有羧酸之酸性纖維素衍生物、在具有羥基之 聚合物加成酸酐而成之物等,而且,在側鏈具有(甲基)丙 烯醯基之高分子聚合物,亦是可舉出的較佳之物。 此等之中,以由(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚 φ 物、或(甲基)丙烯酸苄酯/.(甲基)丙烯酸/其他的單體所構成 的多元共聚物爲特別適合。 此外,已將甲基丙烯酸2-羥基乙酯共聚合之物等亦是 可舉出的有用之物。該聚合物能夠以任意量混合而使用。 除了上述以外,可舉出特開平7- 140654號公報所記載 之(甲基)丙烯酸2-羥基丙酯/聚苯乙烯巨大單體/甲基丙烯 • 酸苄酯/甲基丙烯酸共聚物、2_羥基-3-苯氧基丙烯酸丙酯/ 聚甲基丙烯酸甲酯巨大單體/甲基丙烯酸苄酯/甲基丙烯酸 -32- 200821362 共聚物、甲基丙烯酸2-羥基乙酯/聚苯乙烯巨大單體/甲基 丙烯酸甲酯/甲基丙烯酸共聚物、甲基丙烯酸2-羥基乙酯/ 聚苯乙烯巨大單體/甲基丙烯酸苄酯/甲基丙烯酸共聚物等。 鹼可溶性樹脂的具體性構成單位,以(甲基)丙烯酸與會g, 夠與其共聚合的其他單體之共聚物爲特別適合。 前述能夠與(甲基)丙烯酸共聚合的其他單體可舉出(甲 基)丙烯酸烷酯、(甲基)丙烯酸芳酯、乙烯系化合物等。在 此,烷基及芳基的氫原子亦可以被取代基取代。 ^ 前述(甲基)丙烯酸烷酯、及(甲基)丙烯酸芳酯的具體例 可舉出(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯 酸丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸異丁酯、(甲基) 丙烯酸戊酯、(甲基)丙烯酸己酯、(甲基)丙烯酸辛酯、(甲 基)丙烯酸苯酯、丙烯酸苄酯、丙烯酸甲苯酯、丙烯酸萘酯、 丙烯酸環己酯等。 又,前述乙烯系化合物可舉出例如苯乙烯、α -甲基苯 φ 乙烯、乙烯基甲苯、甲基丙烯酸環氧丙酯、丙烯腈、乙酸 乙烯酯、Ν -乙烯基舭咯啶酮、甲基丙烯酸四氫糠酯、聚苯 乙烯巨大單體、聚甲基丙烯酸甲酯巨大單體、(:仏&lt;&amp;1尺2[在 此,R1係表示氫原子或碳數1〜5的烷基,R2係表示碳數6〜10 的芳香族烴環]、CHarCUiKCOOR3)[在此,R1係表示氫原子 或碳數1〜5的烷基,R3係表示碳數i〜8的烷基或碳數6〜12 的芳烷基]等。 此等能夠共聚合的其他單體能夠單獨使用1種,亦可組 -33- 200821362 合使用2種以上。較佳之能夠共聚合的其他單體係選自 CHfCW、CHa^C^I^MCOOR3)、(甲基)丙烯酸苯酯、(甲基) 丙烯酸苄酯、及苯乙烯之至少1種,以CH^CW、及/或 (:^ = (:(111)((:〇〇113)爲特佳。此等111、112及113係各自與前述 同義。 在光硬化性組成物中之鹼可溶性樹脂的含量,係相對於 該組成物的總固體成分以1〜2 0質量%爲較佳,以2〜1 5質量 %爲更佳,以3〜12質量%爲特佳。 •[光聚合性化合物] 本發明之光硬化性組成物係含有光聚合性化合物之至 少 ~k ° 本發明能夠使用的光聚合性化合物係具有至少一個乙 烯性不飽和雙鍵之加成聚合性化合物,能夠選自具有至少 一個、較佳是二個以上末端乙烯性不飽和鍵之化合物。此 種化合物群組係在該產業領域廣被知悉之物,在本發明, φ 此等沒有特別限定而可以使用。此等係具有例如單體、預 聚物、亦即二聚物、三聚物及低聚物、或是彼等的混合物 和彼等的共聚物等的化學形態。單體及其共聚物可舉出例 如不飽和羧酸(例如,丙烯酸、甲基丙烯酸、伊康酸、巴豆 酸、異巴豆酸、順丁烯二酸等)、或其酯類、醯胺類,以使 用不飽和羧酸與脂肪族多元醇化合物之酯、不飽和羧酸與 脂肪族多元胺化合物之醯胺類爲佳。又,具有羥基或胺基、 氫硫基等親核性取代基之不飽和羧酸酯或醯胺類與單官.能 -34- 200821362 或多官能異氰酸酯類或與環氧類之加成反應物、及與單官 能或多官能羧酸之脫水縮合反應物等亦適合使用。又,異 氰酸酯基或具有環氧基等親電子性取代基之不飽和羧酸酯 或醯胺類與單官能或多官能的醇類、胺類、硫醇類之加成 反應物,而且,具有鹵素基、或對甲苯磺醯氧基等的脫離 性取代基之不飽和羧酸酯或醯胺類與單官能或多官能的醇 類、胺類、硫醇類之取代反應物亦適合。又,其他例子亦 能夠使用已取代爲不飽和膦酸、苯乙烯、乙烯基醚等的化 ® 合物群來代替上述的不飽和羧酸。 脂肪族多元醇化合物與不飽和羧酸之酯的單體之具體 例,丙烯酸酯有乙二醇二丙烯酸酯、三甘醇二丙烯酸酯、 1,3-丁二醇二丙烯酸酯、伸丁二醇二丙烯酸酯、丙二醇二丙 烯酸酯、新戊二醇二丙烯酸酯、三羥甲基丙烷三丙烯酸酯、 三羥甲基丙烷參(丙烯醯氧基丙基)醚、三羥甲基乙烷三丙 烯酸酯、己二醇二丙烯酸酯、1,4-環己烷二醇二丙烯酸酯、 φ 四甘醇二丙烯酸酯、新戊四醇二丙烯酸酯、新戊四醇三丙 烯酸酯、新戊四醇四丙烯酸酯、二新戊四醇二丙烯酸酯、 二新戊四醇六丙烯酸酯、山梨糖醇三丙烯酸酯、山梨糖醇 四丙烯酸酯、山梨糖醇五丙烯酸酯、山梨糖醇六丙烯酸酯、 參(丙烯醯氧基乙基)三聚異氰酸酯、聚酯型丙烯酸酯低聚 物、三聚異氰酸EO改性三丙烯酸酯等。 甲基丙烯酸酯有伸丁二醇二甲基丙烯酸酯、三甘醇二甲 基丙烯酸酯、新戊二醇二甲基丙烯酸酯、三羥甲基丙烷三 -35- 200821362 甲基丙烯酸酯、三羥甲基乙烷三甲基丙烯酸酯、乙二醇二 甲基丙烯酸酯、1,3 -丁二醇二甲基丙烯酸酯、己二醇二甲基 丙烯酸酯、新戊四醇二甲基丙烯酸酯、新戊四醇三甲基丙 烯酸酯、新戊四醇四甲基丙烯酸酯、二新戊四醇二甲基丙 烯酸酯、二新戊四醇六甲基丙烯酸酯、山梨糖醇三甲基丙 烯酸酯、山梨糖醇四甲基丙烯酸酯、雙[對-(3_甲基丙烯醯 氧基-2-羥基丙氧基)苯基]二甲基甲烷、雙_[對_(甲基丙烯醯 氧基乙氧基)苯基]二甲基甲垸等。 伊康酸酯有乙二醇二伊康酸酯、丙二醇二伊康酸酯、 1,3-丁二醇二伊康酸酯、ι,4-丁二醇二伊康酸酯、伸丁二醇 —伊康酸酯、新戊四醇二伊康酸酯、山梨糖醇四伊康酸酯 等。巴豆酸酯有乙二醇二巴豆酸酯、伸丁二醇二巴豆酸酯、 新戊四醇二巴豆酸酯、山梨糖醇四二巴豆酸酯等。異巴豆 酸酯有乙二醇二異巴豆酸酯、新戊四醇二異巴豆酸酯、山 梨糖醇四異巴豆酸酯等。順丁烯二酸酯有乙二醇二順丁烯 二酸酯、三甘醇二順丁烯二酸酯、新戊四醇二順丁烯二酸 酯、山梨糖醇四順丁烯二酸酯等。 其他的酯之例子,例如具有特公昭5卜47 3 34、特開昭 57- 1 9623 1所記載之脂肪族醇系酯類、或特開昭5 9-5240、 特開昭59-5241、特開平2-226149所記載之芳香族系骨格 之物、特開平1 - 1 65 6 1 3所記載之含有胺基之物等亦適合使 用。而且,前述的酯單體亦可以混合物的方式使用。 又,脂肪族多元胺化合物與不飽和羧酸之胺的單體之具 -36 - 200821362 體例,有亞甲基雙-丙烯醯胺、亞甲基雙-甲基丙烯醯胺、 1,6-六亞甲基雙-丙烯醯胺、丨,6_六亞甲基雙-甲基丙烯醯 胺、二伸乙基三胺參丙烯醯胺、苯二甲基雙丙烯醯胺、苯 二甲基雙甲基丙烯醯胺等。其他之較佳醯胺系單體的例 子’可舉出例如特公昭54_2 1 726所記載之具有伸環己基結 構之物。 又’使用異氰酸酯與羥基的加成反應所製造之胺基甲酸 ^ 酯系加成聚合性化物亦佳,此種具體例可舉出例如:在特 公昭48-41708號公報所記載之在1分子具有2個以上異氰 酸酯基之聚異氰酸酯化合物中,加成下述通式(A)所示之含 有羥基的乙烯型單體而成之在1分子中含有2個以上聚合 性乙烯基之乙烯基胺基甲酸酯化合物等。 CH2二C(R34)C〇〇CH2CH(R35)〇H (A) (其中,R34及R35係表示Η或CH3) 又,具有如特開昭5 1 - 3 7 1 9 3號、特公平2 - 3 2 2 9 3號、特 # 公平2- 1 6765號所記載之丙烯酸胺基甲酸酯類、或特公昭 58-498 60號' 特公昭5 6- 1 7654號、特公昭62-394 1 7號、特 公昭62-3 9418號所記載之環氧乙烷系骨架之胺基甲酸酯化 合物類亦佳。而且,藉由使用在特開昭6 3 - 2 7 7 6 5 3號、特 開昭63-260909號、特開平1 - 1 05 23 8號所記載之在分子內 具有胺基結構或硫醚結構之加成聚合性化合物類,能夠得 到感光速度非常優良之光聚合性組成物。 其他的例子可舉出如特開昭 4 8 - 6 4 1 8 3號、特公昭 -37- 200821362 49-43 1 9 1號、特公昭52-30490號,各公報所記載之聚酯型 丙烯酸酯類、環氧樹脂與(甲基)丙烯酸反應而成之環氧丙 烯酸酯類等多官能的丙烯酸酯或甲基丙烯酸酯。又,亦可 舉出特公昭46-43946號、特公平1 -403 37號、特公平1 -40336 號所記載之特定的不飽和化合物、或特開平2-25493號所 記載之乙烯基磺酸系化合物等。又,在某些情況,特開昭 6 1 -22 048號所記載之含有全氟烷基之結構亦適合使用。而 且,亦可使用在日本接著協會會刊第20卷、第7期、第 ^ 300〜308頁(1 984年)所介紹作爲光硬化性單體及低聚物之 物。 關於此等加成聚合性化合物,其結構、單獨使用或倂 用、及添加量等使用方法的詳細,能夠配合最後的光硬化 性組成物的性能設計而任意地設定。例如,能夠從以下的 觀點選擇。 從敏感度而言,以每1分子之不飽和基含量多的結構爲 φ 佳,多半情況係以2官能以上爲佳。又,爲了提高硬化膜 的強度,3官能以上亦佳,而且,藉由倂用不同官能數、 不同聚合性基(例如丙烯酸酯、甲基丙烯酸酯、苯乙烯系化 合物、乙烯基醚系化合物)之物,來調節敏感度及強度之方 法亦是有效的。 又,關於與光硬化性組成物中之其他成分(例如,鹼可 溶性樹脂等的結合劑聚合物、光聚合引發劑、著色劑(顏料)) 之相溶性、分散性,加成聚合化合物的選擇、使用法係重 -38- 200821362 要的因素。例如藉由使用低純度的加成聚合化合物、或倂 用2種以上的加成聚合化合物,會有能夠提高與其他成分 的相溶性之情況。 % 又,選擇特定結構亦能夠得到提高與基板等之緊貼性之 目的。相對於光硬化性組成物中的不揮發性成分,加成聚 合性化合物以5〜70質量%爲較佳,以10〜60質量%的範圍 爲更佳。又,此等可單獨使用,亦能夠倂用2種以上。此 _ 外,從對氧之聚合阻礙大小、解像度、生霧(fog)性、折射 .係數變化、表面黏附性等觀點,加成聚合性化合物的使用 法能夠任意地選擇適當的結構、調配、添加量。 [光聚合引發劑] 本發明的光硬化性組成物含有聚合引發劑之至少一種。 光聚合引發劑可舉出例如特開平57 -6096號公報所記載 之鹵甲基卩f二唑、特公昭59- 1 28 1號公報、特開昭5 3 - 1 3 3428 號公報等所記載之鹵甲基-s-三畊等活性鹵素化合物、美國 • 專利USP-43 1 879 1、歐洲專利公開EP-8 805 0A等各說明書所 記載之縮酮、縮醛、或苯偶姻烷基醚類等的芳香族羰基化 合物、美國專利USP-4 199420說明書所記載之二苯基酮類 等的芳香族酮化合物、Fr-245 674 1說明書所記載之(噻)咕噸 酮((Thio) xanthone)類或吖啶類化合物、特開平1 0-62986號 公報所記載之香豆素類或咯吩二聚物類等的化合物、特開 平8-0 1 5 5 2 1號公報等的毓有機硼錯合物等等。 其中,本發明的光硬化性組成物之光聚合引發劑’以含 -39- 200821362 有選自乙醯苯系化合物、縮酮系化合物、二苯基酮系化合 物、苯偶姻系化合物、苯甲醯系化合物、咕噸酮系化合物、 三阱系化合物、鹵甲基卩f二唑系化合物、吖啶類系化合物、 香豆素類系化合物、咯吩二聚物類系化合物、二咪唑系化 合物、肟系化合物等之光聚合引發劑爲更佳,以含有選自 三阱系化合物、咯吩二聚物類系化合物、肟系化合物等之 光聚合引發劑爲特佳。 前述乙醯苯系的光聚合引發劑可適合舉出例如 2,2-二 乙氧基乙醯苯、對二甲基胺基乙醯苯、2-羥基-2-甲基-1胃苯 基-丙烷-1-酮、對二甲基胺基乙醯苯、4’ -異丙基-2-羥基-2- 甲基-丙醯苯等。 前述縮酮系的光聚合引發劑可適合舉出例如苄基二甲 基縮酮、苄基- /3 -甲氧基乙基縮-等。 前述二苯基酮系的光聚合引發劑可適合舉出例如二苯 基酮、4,4’ -(雙二甲基胺基)二苯基酮、4,4’ -(雙二乙基胺 基)二苯基酮、4,4’ -二氯二苯基酮、1-羥基-環己基-苯基- 酮、2-苄基-2-二甲胺基-1-(4-味啉苯基)-丁酮-1、2-甲苯基 -2-二甲胺基-1-(4-味啉苯基)-丁酮-1、2-甲基-1-[4-(甲硫基) 苯基]_ 2 -味啉丙酮-1等。 前述苯偶姻系化合物或苯甲醯系的光聚合引發劑可適 合舉出例如苯偶姻異丙基醚、苯偶姻異丁基醚、苯偶姻甲 基醚、鄰苯甲醯基苯甲酸甲酯等。 前述咕噸酮(xanthone)系的光聚合引發劑可適合舉出例 -40- 200821362 如二乙基噻咕噸酮、二異丙基噻咕噸酮、、一異丙基噻咕噸 酮、氯噻咕噸酮等。 前述三畊系的光聚合引發劑可適合舉出例如2,4-雙(三 氯甲基)-6-對甲氧基苯基三畊、2,4-雙(三氯甲基)-6-對甲 氧基苯乙烯基-s-三畊、2,4-雙(三氯甲基)-6-(1-對二甲胺基 苯基)-1,3-丁二烯基-s-三阱、2,4-雙(三氯甲基)-6-聯苯基- s-三阱、2,4-雙(三氯甲基)-6-(對甲基聯苯基)-s-三阱、對羥乙 氧基苯乙烯基-2,6-二(三氯甲基)-s-三畊、甲氧基苯乙烯基 -2,6-二(三氯甲基)-8-三畊'3,4-二甲氧基苯乙烯基-2,6-二 (三氯甲基)-8-三哄、4-苯并氧環戊烷-2,6-二(三氯甲基)-5-三畊、4-(鄰-溴-對-Ν,Ν-(二乙氧基羰基胺基)-苯基)-2,6-二 (氯甲基)-s-三畊、4-(對-Ν,Ν-(二乙氧基羰基胺基苯 基)-2,6-二(氯甲基)-s-三畊等。 前述鹵甲基噚二唑系的光聚合引發劑可適合舉出例如 2-三氯甲基-5-苯乙烯基-1,3,4-噚二唑、2-三氯甲基-5-(氰基 φ 苯乙烯基)-1,3,4-噚二唑、2-三氯甲基-5-(萘-卜基)-1,3,4-噚二唑、2-三氯甲基-5-(4-苯乙烯基)苯乙烯基-1,3,4-噚二唑 等。 前述吖啶類系的光聚合引發劑可適合舉出例如9-苯基 吖啶、1,7-雙(9-吖啶基)庚烷等。 前述香豆素類系的光聚合引發劑可適合舉出例如3 -甲 基-5-胺基- ((s-三阱-2-基)胺基)-3-苯基香豆素、3-氯-5-二乙 胺基-((s-三阱-2-基)胺基)-3·苯基香豆素、3-丁基-5-二甲胺 -41- 200821362 基-((s-三哄-2-基)胺基)_3-苯基香豆素等。 前述咯吩二聚物類系的光聚合引發劑可適合舉出例如 2-(鄰氯苯基)-4,5 -二苯基咪唑基二聚物、2-(鄰甲氧基苯 基)-4,5·二苯基咪唑基二聚物、2_(2,4_二甲氧基苯基4,5-二苯基咪唑基二聚物等。 前述二咪唑系的光聚合引發劑可適合舉出例如2_氫硫 基苯并咪唑、2,2’ -苯并噻唑基二硫醚等。 前述肟系的光聚合引發劑可舉出例如丨-苯基丙烷 二酮-2-(鄰乙氧基羰基)肟、鄰苯甲醯基_4’ _(苯并氫硫基) 苯甲醯基-己基-酮肟,而且,可舉出LC.S. Perkin II (197 9 年)第 1 65 3- 1 660 頁)、JLC.S· Perkin II (1 979 年)第 156-162 頁、光聚合物科學及技術期刊(J ournal of Photopolymer Science and Technology)( 1 995 年)第 202-232 頁、特開 2000-66385號公報、特開 2000-80068號公報、特表 2004-534797號公報等所記載之化合物。 上述以外的光聚合引發劑可舉出2,4,6-三甲基苯基羰 基-二苯基膦醯氧化物、六氟偶磷-三烷基苯基鐵鹽等。 本發明能夠使用的光聚合引發劑,未限定於上述的光聚 合引發劑,亦能夠使用其他眾所周知之物。可舉出例如美 國專利第2,367,660號說明書所記載之連位聚縮酮糖醛基 化合物、美國專利第2,367,66 1號及第2,367,670號說明書 所記載之α -羰基化合物、美國專利第2,448,828號說明書 所記載之偶姻醚(acyloin ether)、美國專利第2,722,5 1 2號說 -42- 200821362 明書所記載之被α -烴取代而成的芳香族偶姻化合物、美國 專利第3,〇46,127號及第2,951,7 5 8號說明書所記載之多核 化合物、美國專利第3,549,3 67號說明書所記載之三烯丙基 咪唑二聚物/對胺基苯基酮的組合、特公昭5 1 -4 8 5 1 6號公報 所記載之苯并噻唑系化合物/三鹵甲基-S-三畊系化合物等。 又,亦可倂用此等的光聚合引發劑。 在光硬化性組成物中之光聚合引發劑的含量,係相對於 該組成物的總固體成分以 0 .1〜1 5.0質量%爲較佳,以 0.5〜10.0質量%爲更佳。光聚合引發劑的含量在該範圍內 時,能夠使聚合反應良好地進行而形成強度良好的膜。 爲了提高光聚合引發劑(自由基引發劑)的自由基產生 效率、感光波長的長波長化之目的,本發明的光硬化性組 成物亦可含有增感劑。 本發明能夠使用的增慼劑,以能夠藉由電子移動機構或 能量移動機構來使自由基引發劑增加敏感度之物爲佳。 本發明能夠使用的增感劑可舉出屬於以下列舉之化合 物類,且在3 0 0奈米〜4 5 0奈米的波長區域具有吸收波長之 物。 較佳之增感劑的例子,可舉出屬於以下之化合物類且在 3 3 0奈米〜45Q奈米的波長區域具有吸收波長之物。 例如多核芳香族類(例如’菲、蒽、芘、茈、聯伸三苯 (tnphenylene)、9,10-二烷氧基蒽)、咕噸類(例如,螢光素、 曙紅、紅徽素、若丹明B、玫瑰紅)、曝咕囉酬類(異丙基_ -43- 200821362 咕噸酮、二乙基噻咕噸酮、氯噻咕噸酮)、花青苷類(例如 噻碳花青、噚碳花青)、部花青素類(如部花青、碳部花青 素)、酞青類、噻阱類(例如硫僅、亞甲藍、甲苯胺藍)、吖 啶類(例如吖啶橙、氯黃素、吖啶黃素)、蒽醌類(例如蒽醌)、 角鯊鑰類(例如角鯊鑰)、吖啶橙、香豆素類(例如,二乙 胺基-4-甲基香豆素)、酮香豆素、啡噻畊類、啡哄類、苯乙 烯基苯類、偶氮化合物、二苯基甲烷、三苯基甲烷、二苯 乙烯苯類、咔唑類、紫菜鹼、螺化合物、喹吖酮、靛藍、 苯乙烯、吡啶鑰化合物、甲撐吡咯化合物、吡唑三唑化合 物、苯并噻唑化合物、巴比士酸衍生物、硫代巴比士酸衍 生物、乙醯苯、二苯基酮 '噻咕噸酮、米其勒酮等芳香族 酮化合物、及N-芳基噚唑啶酮等雜環化合物等。 本發明的光硬化性組成物以含有共增感劑爲佳。本發明 的光硬化性組成物之共增感劑具有更提升增感色料或引發 劑對活性放射線的敏感度,或是抑制氧對聚合性化合物的 φ 聚合阻礙等作用。 此種共增感劑可舉出例如胺類、例如M.R. Sander等著 「聚合物學會期刊(Journal of Polymer Society)」第10卷第 3173頁( 1 972年)、特公昭44-20 1 89號公報、特開昭51-82102 號公報、特開昭52- 1 34692號公報、特開昭5 9- 1 3 8205號公 報、特開昭60- 84305號公報、特開昭62- 1 85 37號公報、特 開昭64-33104號公報、硏究發表(Research Disclosure)第 3 3 825號所記載之化合物等,具體上,可舉出三乙醇胺、對 -44- 200821362 二甲胺基苯甲酸乙酯、對甲醯基二甲基苯胺、對甲硫基二 甲基苯胺等。 共增感劑之另外例子係硫醇及硫醚類,可舉出例如特開 昭53-702號公報、特公昭55_5〇〇8〇6號公報、特開平 5 - 1 42772號公報所記載之硫醇化合物、特開昭5 6-7 5 643號 公報之二硫醚化合物等,具體上可舉出2-氫硫基苯并噻 口坐、2 -氫硫基苯并腭嗤、2 -氫硫基苯并咪π坐、2-氫硫基- 4(3H)-喹唑啉、Θ -氫硫基萘等。 又’其他的例子可舉出胺基酸化合物(例如,N-苯基甘 胺酸等)、特公昭48-42965號公報所記載之有機金屬化合物 (例如乙酸三丁基錫等)、特公昭55-344 1 4號公報所記載之 氫給予體、特開平6-308727號公報所記載之硫黃化合物(例 如三聚硫甲醛(trithiane)等)等。 從藉由聚合成長速度及鏈轉移的平衡來提升硬化速度 之觀點,相對於光硬化性組成物之總固體成分的質量,此 φ 等共增感劑的含量以0.1〜30質量%的範圍爲佳,以1〜25質 量%的範圍爲較佳,以0.5 ~20質量%的範圍爲更佳。 接著,說明上述以外的成分。 [溶劑] 本發明的光硬化性組成物係通常能與上述成分一起使 用溶劑而適當地調製。 作爲溶劑之酯類可舉出例如乙酸乙酯、乙酸正丁酯、乙 酸異丁酯、甲酸戊酯、乙酸異戊酯、乙酸異丁酯、丙酸丁 -45- 200821362 酯、丁酸異丙酯、丁酸乙酯、丁酸丁酯、烷基酯類、乳酸 甲酯、乳酸乙酯、氧基乙酸甲酯、氧基乙酸乙酯、氧基乙 酸丁酯、甲氧基乙酸甲酯、甲氧基乙酸乙酯、甲氧基乙酸 丁酯、乙氧基乙酸甲酯、乙氧基乙酸乙酯、和3 -氧基丙酸 甲酯及3 -氧基丙酸乙酯等的3 -氧基丙酸烷酯類(·例如,3 -甲氧基丙酸甲酯、3 -甲氧基丙酸乙酯、3 -乙氧基丙酸甲酯、 3 -乙氧基丙酸乙酯)、和2 -氧基丙酸甲酯、2 -氧基丙酸乙酯、 及2-氧基丙酸丙酯等的2-氧基丙酸烷酯(例如2_甲氧基丙 ^ 酸甲酯、2 -甲氧基丙酸乙酯、2 -甲氧基丙酸丙酯、2 -乙氧基 丙酸甲酯、2-乙氧基丙酸乙酯' 2_氧基-2-甲基丙酸甲酯、 2-氧基-2-甲基丙酸乙酯、2-甲氧基-2-甲基丙酸甲酯、2-乙 氧基-2-甲基丙酸乙酯)、和丙酮酸甲酯、丙酮酸乙酯、丙酮 酸丙酯、乙醯乙酸甲酯、乙醯乙酸乙酯、2-側氧基酞酸甲 酯、2-側氧基酞酸乙酯等; 醚類可舉出例如二甘醇二甲基醚、四氫呋喃、乙二醇一 φ 甲基醚、乙二醇一乙基醚、甲基賽路蘇乙酸酯、乙基賽路 蘇乙酸酯、二甘醇一甲基醚、二甘醇一乙基醚、二甘醇一 丁基醚、丙二醇一甲基醚乙酸酯(在本說明書中,亦稱爲2-乙醯氧基-1-甲氧基丙烷)、丙二醇一乙基醚乙酸酯、丙二醇 一丙基醚乙酸酯等; 酮類可舉出例如甲基乙基酮、環己酮、2-庚酮、3-庚酮 等; 芳香族烴類可舉出例如甲苯、二甲苯等。 -46 - 200821362 此等之中,以3 -乙氧基丙酸甲酯、3 -乙氧基丙酸乙酯、 乙基賽路蘇丁乙酸酯、乳酸乙酯、二甘醇二甲基醚、乙酸 丁酯、3-甲氧基丙酸甲酯、2-庚酮、環己酮、乙基卡必醇 乙酸酯、丁基卡必醇乙酸酯、丙二醇一甲基醚乙酸酯等爲 佳。 溶劑可單獨使用,亦可組合2種以上而使用。 [其他成分] 0 本發明的光硬化性組成物能夠按照必要含有氟系有機 化合物、防止熱聚合劑、塡料、特定顏料分散劑、及前述 鹼可溶性樹脂以外的高分子化合物、界面活性劑、緊貼促 進劑、抗氧化劑、紫外線吸收劑、抗凝聚劑等各種添加劑。 &lt;氟系有機化合物&gt; 藉由含有氟系有機化合物,能夠改善作爲塗布液時之液 體特性(特別是流動性),能夠改善塗布厚度的均勻性或省 液性。亦即,因爲使基板與塗布液之界面張力降低來改善 • 對基板的潤濕性,提升對基板的塗布性,所以即使在使用 少量的液量形成數微米左右的薄膜的情況下,就能夠形成 厚度不均小之均勻厚度的膜而言係有效的。 氟系有機化合物的含有率以3〜40質量%爲較佳,以5〜30 質量%爲更佳,以7〜25質量%爲特佳。氟含有率在此範圍 內時,就塗布厚度均勻性或省液性而言係有效的,且對組 成物中之溶解性亦良好。 氟系有機化合物可舉出例如MEGAFAC F171、同F172、 -47- 200821362 同 F173、同 F177、同 F141、同 F142、同 F143、同 F144、 同R30、同F437(以上,大日本油墨化學工業(股)製)、 FRORAD FC430、同 FC431、同 FC17U以上,住友 3M(股) 製)、SAFRON S-382、同 SC-101、同 SC-103、同 SC-104、 同 SC-105、同 SC 1068、同 SC-381、同 SC- 3 8 3、同 S 3 93、 同KH-4〇(以上,旭硝子(股)製)_ ° 特別是例如使塗布形成的塗布膜薄化時’氟系有機化合 物對防止塗布不均或厚度不均係有效的。又’在容易引起 ^ 缺液的狹縫塗布方面亦是有效的。 相對於顏料分散組成物或光硬化性組成物的總質量’氟 系有機化合物的添加量以0.001〜2.0質量%爲較佳’以 0.005〜1.0質量%爲更佳。 &lt;熱聚合引發劑&gt; 在本發明的光硬化性組成物含有熱聚合引發劑亦是有 效的。熱聚合引發劑可舉出例如各種偶氮系化合物、過氧 φ 化物系化合物,前述偶氮系化合物可舉出偶氮雙系化合 物,前述過氧化物系化合物可舉出過氧化酮、過氧化縮酮、 過氧化氫、二烷基過氧化物、過氧化二醯、過氧化酯、過 氧化二碳酸酯等。 &lt;界面活性劑〉 從改良塗布性的觀點,本發明的光硬化性組成物以使用 各種界面活性劑而構成爲佳,能夠使用非離子系、陽離子 系、陰離子系的各種界面活性劑。其中,以非離子系界面 -48- 200821362 活性劑且具有全氟烷基之氟系界面活性劑爲佳。 氟系界面活性劑的具體例可舉出例如大日本油墨化學 工業(股)製的 MEGAFAC(註冊商標)系列、3M公司製的 FLORAD(註冊商標)系歹!J等。 上述以外,光硬化性組成物中之添加物的具體例可舉出 玻璃、氧化鋁等塡料;伊康酸共聚物、巴豆酸共聚物、順 丁烯二酸共聚物、部分酯化順丁烯二酸共聚物、酸性纖維 素衍生物、使具有羥基之聚合物加成酸酐之物、醇可溶性 耐綸、由雙酚A與表氯醇所形成的苯氧樹脂等的鹼可溶性 樹脂;非離子系、陽離子系、陰離子系等界面活性劑、具 體上有酞青衍生物(市售品日?1^八-745 (森下產業公司製)); 有機矽氧烷聚合物KP341 (信越化學工業公司製)、(甲基)丙 烯酸系(共)聚合物POLYFRO No.75、No.90、No.95(共榮社 油脂化學工業公司製)、W001 (裕商公司製)等陽離子界面活 性劑; φ 其他添加物等可舉出例如聚氧乙烯月桂基醚、聚氧乙烯 硬脂基醚、聚氧乙烯油醯基醚、聚氧乙烯辛基苯基醚、聚 氧乙烯壬基苯基醚、聚乙二醇二月桂酸酯、聚乙二醇二硬 脂酸酯、山梨糖醇酐脂肪酸酯(BASF製的PLURONIC L 1 0、 L31、L61、L6 2、l〇R5、17R2、25R2、TETRONIC 304、701、 7 04、901、904、150R1等的非離子系界面活性劑;W004、 W005、W017(裕商公司製)等陰離子系界面活性劑; EFKA-46、EFKA-47、EFKA-47EA、EFKA POLYMER 100、 -49- 200821362 EFKA POLYMER400 、 EFKA POLYMER401 、 EFKA POLYMER450(以上森下產業公司製)、DISPERSAID6、 DISPERSAID8 、 DISPERSAID15 、 DISPERSAID9100 (SANNOPCO公司製)等的高分子分散劑;SOLUSPAS3000 &gt; 5000、 9000、 12000、 13240、 13940、 17000、 24000、 26000、 28000等各種 SOLUSPAS 分散齊ί (ZENECA 公司製); ADEKAPLURONIC L31、F38、L42、L44、L61、L64、F68、 L7 2、P95、F7 7、P84、F87、P94、L101、P103、F108、L121、 P-123(旭電化公司製)及ISONET S-20(三洋化成公司製); 2-(3-第三丁基-5-甲基-2-羥苯基)-5-氯苯并三唑、烷氧基二 苯基酮等的紫外線吸收劑;及聚丙烯酸鈉等抗凝聚劑。 又,爲了謀求促進未硬化部的鹼溶解性,來更提升光硬 化性組成物的顯影性時,能夠在光硬化性組成物進行添加 有機羧酸,較佳是分子量1000以下的低分子量有機羧酸。 ’ 具體上可舉出例如甲酸、乙酸、丙酸、丁酸、戊酸、三甲 φ 基乙酸、己酸、二乙基乙酸、庚酸、辛酸等的脂肪族一羧 酸;草酸、丙二酸、琥珀酸、戊二酸、己二酸、庚二酸、 辛二酸、壬二酸、癸二酸、十三烷二酸、甲基丙二酸、乙 基丙二酸、二甲基丙二酸、甲基琥珀酸、四甲基琥珀酸、 檸康酸等脂肪族二羧酸;1,2,3-丙三甲酸、烏頭酸、樟腦三 酸等脂肪族三羧酸;苯甲酸·、苯乙酸、小茴香酸、二甲苯 酸、3,5-二甲基苯甲酸等芳香族一羧酸;酞酸、異酞酸、對 酞酸、偏苯三甲酸、均苯三甲酸、偏苯四甲酸、焦蜜石酸 -50- 200821362 等芳香族聚羧酸;苯基乙酸、氫阿托酸、氫桂皮酸、苦杏 仁酸、苯基琥珀酸、阿托酸、桂皮酸、桂皮酸甲酯、桂皮 酸苄酯、亞桂皮基乙酸、香豆酸、繳形酸等其他的羧酸。 (防止熱聚合劑) 在本發明之光硬化性組成物,以更添加防止熱聚合劑爲 佳,例如氫醌、對甲氧基苯酚、二-第三丁基-對甲酚、五 倍子酚、第三丁基兒茶酚、苯醌、4,4’ -硫代雙(3-甲基-6- _ 第三丁基苯酚)、2,2’ -亞甲基雙(4-甲基-6·第三丁基苯 酚)、2-氫硫基苯并咪唑等係有用的。 本發明的光硬化性組成物能夠在前述之本發明的顏料 分散組成物中含有(較佳是與溶劑一同含有)鹼可溶性樹 脂、光聚合性化合物、及光聚合引發劑,並按照必要混合 界面活性劑等添加劑來調製。 &lt;彩色濾光片及其製法&gt; 本發明的彩色濾光片係藉由使用前述之本發明的光硬 • 化性組成物在玻璃等基板上形成經著色的膜(著色圖案)來 製造。 具體上,係將本發明之光硬化性組成物直接或透過其他 的層賦予(較佳是藉由旋轉塗布、狹縫塗布、流延塗布、輥 塗布等塗布方法來塗布)在基板上,來形成感光性膜。對所 形成的感光性膜上,透過規定的光罩圖案進行曝光,並在 曝光後使用顯影液除去未硬化部,來形成各色(例如3色或 4色)的著色圖案(例如著色像素),能夠製造最佳的彩色濾 -51- 200821362 光片。 · 藉此,能夠以製程上的困難性少、高品質、且低成本的 方式製造使用於液晶顯示元件或固體攝像元件之彩色濾光 此時,曝光所使用的放射線以g射線、h射線、1射線、 j射線等紫外線爲特佳。 賦予(較佳是塗布)在基板上之由本發明的光硬化性組 成物形成的膜,其乾燥(預烘烤)能夠使用加熱板、烘箱等 ® 以在50°C〜140°C的溫度範圍以10秒〜300秒的條件來進行。 顯影使曝光後之未硬化部溶出至顯影液\而只有使硬化 部殘留。顯影溫度通常爲20°C〜30°C,顯影時間爲20秒〜90 秒。 顯影液若是能夠溶解在未硬化部之光硬化性組成物的 膜、且另一方面不會溶解硬化部時,能夠使用任何物。具 體上能夠使用各種有機溶劑的組合或鹼性水溶液。 φ 前述有機溶劑可舉出在調製本發明的顏料分散組成物 或光硬化性組成物時所列舉之能夠使用之前述的有機溶劑 或溶劑。 前述鹼性水溶液可舉出例如將氫氧化鈉、氫氧化鉀、碳 酸鈉、碳酸氫鈉、矽酸鈉、偏矽酸鈉、氨水、乙胺、二乙 胺、二甲基乙醇胺、氫氧化四甲銨、氫氧化四乙銨、膽鹼、 吡咯、哌啶、1,8-二氮雜雙環-[5,4,0]-7-十一烯等鹼性化合 物,以濃度爲0 · 00 1〜1 0質量%、較佳是〇 · 〇 1〜1質量%的方 -52 - 200821362 式溶解而成的驗性水溶液。 又,將鹼性水溶液作爲顯影液使用時,通常係在顯影後 使用水進行洗淨(沖洗)。 在顯影後係洗淨除去剩餘的顯影液,並施行乾燥後,通 常在100°C〜240°C的溫度施行加熱處理(後烘烤)。前述後烘 烤係用以使硬化完全之顯影後加熱,通常進行約2 0 0 °C〜2 5 0 °C的加熱(硬化烘烤)。該後烘烤處理係對顯影後的塗布膜能 以上述條件使用加熱板或對流烘箱(熱風循環式乾燥機)、高 頻加熱機等加熱手段並藉由連續式或分批式來進行。 藉由使上述操作配合需要的色相數,依照各色順序重複 進行,能夠製造形成有硬化膜(複數色著色而成)而構成的 彩色濾光片。 在基材上賦予本發明的光硬化性組成物而形成膜時,膜 的乾燥厚度通常爲0.3微米〜5.0微米,以0.5微米〜3.5微米 爲佳,以1.0微米〜2.5微米爲最佳。 φ 基板可舉出例如液晶顯示元件所使用的無鹼玻璃、鈉鈣 玻璃、派勒斯(PYREX)(註冊商標)玻璃、石英玻璃、及在此 等黏附透明導電膜而成之物、或固體攝像元件等所使用之 光電轉換元件基板、例如矽基板等、和塑膠基板。在此等 基板上,通常形成有黑色條紋用以將各像素隔離。 在塑膠基板,以其表面具有氣體阻障層及/或耐溶劑性 層爲佳。 在基板上透過其他的層而賦予光硬化性組成物時,其他 -53- 200821362 的層可舉出氣體阻障層、耐溶劑性層等。 上述主要是以彩色濾光片的用途爲中心,來說明本發明 顏料分散組成物及光硬化性組成物的用途,但是亦可應用 於形成黑色矩陣用以隔離構成彩色濾光片的各著色像素。 黑色矩陣能夠藉由使用以碳黑、鈦黑等黑色顏料作爲顏 料之本發明的光硬化性組成物(顏料分散組成物),並進行 圖案曝光、顯影,隨後按照必要更進行後烘烤用以促進膜 的硬化來形成。 [實施例] 以下,藉由實施例來更具體地說明本發明,但是只要未 脫離本發明的主旨,則本發明並非限定於以下的實施例。 又,若未事先告知,「份」係表示「質量份」。 [合成例1] (單體-1的合成) . 將9.5 1份2-胺基嘧啶溶解在30份吡啶中,並加熱至 φ 45 °C。對此,滴加17.1份2-甲基丙烯醯氧基異氰酸乙酯, 在5 0 °C更進行加熱攪拌5小時。一邊攪拌該反應液一邊注 入200份蒸餾水中,過濾分開所得到的析出物並洗淨,得 到23.8份單體1(前述之例示化合物2)。 (聚合物1的合成) 將5.0份前述單體1、37.5份在末端具有甲基丙烯醯基 之聚甲基丙烯酸甲酯(AA-6 :東亞合成公司製)、7.5份甲基 丙烯酸、及116.7份1-甲氧基-2-丙醇’導入已氮氣取代之 -54- 200821362 三口燒瓶中,使用攪拌機(新東科學(股):THREE ONE MOTOR)攪拌,一邊使氮氣流入燒瓶內一邊力口熱升溫至78 °C。對其添加0.1份二甲基-2,2’ -偶氮雙(2-丙酸甲酯)(和 光純藥(股)製「V-601」),在78t:進行加熱攪拌2小時。2 小時後,更添加〇·1份V-601並加熱攪拌3小時,得到聚 合物1(前述之例示化合物(2))的30%溶液。 [合成例2] (單體-2的合成) 將13.3份2-胺基苯并咪唑溶解在30份吡啶中,並加熱 至45 °C。對此,滴加17.1份2-甲基丙烯醯氧基異氰酸乙酯, 在50°C更進行加熱攪拌5小時。一邊攪拌該反應液一邊注 入200份蒸餾水中,過濾分開所得到的析出物並洗淨,得 到27.3份單體2(前述之例示化合物M-4)。 (聚合物2的合成) 將5.0份前述單體2、37.5份在末端具有甲基丙烯醯基 φ 之聚甲基丙烯酸甲酯(AA-6 :東亞合成公司製)、7.5份甲基 丙烯酸、及116.7份1-甲氧基-2-丙醇,導入已氮氣取代之 三口燒瓶中,使用攪拌機(新東科學(股):THREE ONE MOTOR)攪拌,一邊使氮氣流入燒瓶內一邊力口熱升溫至78 °C。對其添加〇·1份二甲基-2,2’ -偶氮雙(2-丙酸甲酯)(和 光純藥(股)製「V-601」),在78°(:進行加熱攪拌2小時。2 小時後,更添加〇 · 1份V - 6 01並加熱攪拌3小時,得到聚 合物2 (前述之例示化合物(6))的3 0 %溶液。 -55- 200821362 [合成例3] (聚合物3的合成) 將5.0份前述單體2、37.5份在末端具有甲基丙烯醯基 之聚甲基丙烯酸甲酯(AA-6 :東亞合成公司製)、7.5份甲基 丙烯酸、0.90份正十二烷基硫醇、及116.7份1-甲氧基-2-丙醇,導入已氮氣取代之三口燒瓶中,使用攪拌機(新東科 學(股)·· THREE ONE MOT OR)攪拌,一邊使氮氣流入燒瓶內 一邊加熱升溫至75 °C。對其添加0.26份二甲基-2,2’ -偶氮 雙(2-丙酸甲酯)(和光純藥(股)製「V-601」),在75°C進行 加熱攪拌3小時。更添加0.26份V-601並加熱攪拌3小時 後,再次添加0.26份V-601並加熱攪拌3小時,得到聚合 物3(前述之例示化合物(17))的30%溶液。 [合成例4] (聚合物4的合成) 將5.0份前述單體2、40.0份在末端具有甲基丙烯醯基 φ 之聚苯乙烯(AS-6 :東亞合成公司製)、5.〇份甲基丙烯酸、 0·76份正十二烷基硫醇、及116.7份1-甲氧基-2-丙醇,導 入已氮氣取代之三口燒瓶中,使用攪拌機(新東科學(股): THREE ONE MOTOR)攪拌,一邊使氮氣·流入燒瓶內一邊加 熱升溫至75°C。對其添加〇·22份二甲基-2,2’ -偶氮雙(2- 丙酸甲酯)(和光純藥(股)製「V-601」),在75°C進行加熱攪 拌3小時。更添加〇. 2 2份V - 6 0 1並加熱攪拌3小時後,再 次添加0 · 2 2份V - 6 0 1並加熱攪拌3小時,得到聚合物4 (前 -56 - 200821362 述之例示化合物(1 8))的3 0 %溶液。 [合成例5] (聚合物5的合成) 將4.0份前述單體2、38.5份在末端具有甲基丙烯醯基 之聚甲基丙烯酸甲酯(ΑΑ-6 :東亞合成公司製)、7.5份甲基 丙烯酸2-羥基乙酯的琥珀酸酐加成物(新中村化學(股)製、 NK ESTER SA:下述結構)、0.43份正十二烷基硫醇、及1 16.7 份1-甲氧基-2 -丙醇,導入已氮氣取代之二口燒瓶中,使用 攪拌機(新東科學(股):THREE ONE MOTOR)攪拌,一邊使 氮氣流入燒瓶內一邊加熱升溫至75t。對其添加0.12份二 甲基-2,2 ’ -偶氮雙(2-丙酸甲酯)(和光純藥(股)製 「V-601」)’在75 °C進行加熱攪拌3小時。更添加0.12份 V-601並加熱攪拌3小時後,再次添加〇. 12份V-601並加 熱攪拌3小時,得到聚合物5(前述之例示化合物(19))的30% 溶液。- R12-S-fcH2-G^H h 〇 T r In the formula (2), R11 and R13 each independently represent a hydrogen atom or a methyl group. R12 represents a linking group containing an alkylene group having 1 to 12 carbon atoms, and the linking group may be an alkylene group having 1 to 12 carbon atoms, or may be a plurality of alkylene groups permeating an ester bond or an ether. A bond, a guanamine bond, or the like. Preferably, R12 is an alkylene group having 1 to 4 carbon atoms or an alkylene group having 1 to 4 carbon atoms which is bonded through an ester bond. The alkylene group represented by R12 may also have a more substituent (Example -16 - 200821362 such as a hydroxyl group). Y represents a phenyl group having no substituent, a phenyl group having 1 alkyl group having 1 to 4 carbon atoms, or -COOR14. Here, R14 represents an alkyl group having 1 to 6 carbon atoms, a phenyl group or an aralkyl group having 7 to 10 carbon atoms. γ is preferably phenyl or -COOR14, wherein R14 represents an alkyl group having 1 to 12 carbon atoms. The q system represents an integer of 20 to 200. In the present invention, preferred examples of the polymerizable oligomer (large monomer) which can be used for synthesizing a specific pigment dispersant include polymethyl (meth) acrylate and poly(butyl) methacrylate. And poly(meth)acrylic acid isobutyl ester, and a polymer bonded to the (meth) propyl group at the end of one molecule of polystyrene. The polymerizable oligomer which can be obtained in the market is a polystyrene oligomer having a terminal methacrylic acid (Mn = 6000, trade name, AS-6, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.) a polymethacrylate oligomer having a terminal methacrylic acid (Mn = 6000, trade name: AA-6, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), and a terminal methacrylic acid polycondensation N-butyl methacrylate oligomer φ (Μη = 6〇00, trade name: AB-6, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.). The specific pigment dispersant of the present invention preferably contains a copolymerization unit derived from a monomer having an acid group. Since the specific pigment dispersant further contains a copolymerization unit derived from a monomer having an acid group, for example, when the pigment dispersion composition of the present invention is patterned by photolithography, the pattern formability can be further improved. Examples of the monomer having an acid group include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid, and cinnamic acid; maleic acid, -17-200821362 maleic anhydride, and anti- Unsaturated dicarboxylic acid or anhydride thereof such as butenedioic acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid; unsaturated polycarboxylic acid or anhydride thereof having a valence of 3 or more; amber Acid mono(2-propenyloxyethyl) ester, succinic acid mono(2-methylpropenyloxyethyl) ester, decanoic acid mono(2-propenyloxyethyl) ester, citric acid mono ( Monomethyl [(meth) propylene decyloxyalkyl] ester of a divalent or higher polyvalent carboxylic acid such as 2,methacryloyl fluorenyl-ethylidene ethyl ester; ω-carboxy-polycaprolactone monoacrylate, carboxyl group - A (meth) acrylate such as a polycaprolactone-methyl propyl acrylate or a terminal carboxypolymer. The specific pigment dispersant of the present invention may further contain a copolymerizable ethylene-based monomer as a copolymerization component insofar as the effect is not impaired. Here, the vinyl type monomer can be used without particular limitation, for example, (meth) acrylates, crotonates, vinyl esters, maleic acid diesters, and fumaric acid diesters. Preferably, it is a class of Ikonic acid diesters, (meth) acrylamides, vinyl ethers, esters of vinyl alcohol, styrenes, (meth)acrylonitrile, and the like. Specific examples of such a vinyl monomer include, for example, a compound of φ. Examples of the (meth) acrylates include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, and (methyl). N-butyl acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl (meth)acrylate, tert-butyl (meth)acrylate Cyclohexyl ester, 2-ethylhexyl (meth)acrylate, third octyl (meth)acrylate, dodecyl (meth)acrylate, octadecyl (meth)acrylate, (methyl) Ethyloxyethyl acrylate, (methyl) -18- 200821362 A 2 bis 2-(acid olefinic propylene propylene 3⁄4) 3⁄4) E methyl / 1 \ , ester ester ethyl ethyl oxy oxy diacetate 2 ene Acid propylene propyl ketone ketone ketone — 酉 酉 ( 酉 酉 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 乙烯基 酉 酉Ester, benzyl (meth) acrylate, diethylene glycol monomethyl ether (meth) acrylate, diethylene glycol monoethyl ether (meth) acrylate, (methyl) propyl Triethylene glycol monomethyl ether, triethylene glycol monoethyl ether (meth)acrylate, polyethylene glycol monomethyl ether (meth)acrylate, polyethylene glycol monoethyl ether (meth)acrylate , 々-phenoxyethoxyethyl (meth)acrylate, nonylphenoxy polyethylene glycol (meth)acrylate, dicyclopentenyl (meth)acrylate, bicyclo(meth)acrylate Pentenyloxyethyl ester, trifluoroethyl (meth)acrylate, octafluoropentyl (meth)acrylate, perfluorooctylethyl (meth)acrylate, dicyclopentanyl (meth)acrylate, Tribromophenyl methacrylate, tribromophenoxyethyl (meth) acrylate, etc. Further, in the present specification, any one or both of "acryloyl group and methacryl group" will be described. In the case of "(meth)acrylyl group", examples of the crotonate include butyl crotonate and hexyl crotonate, etc. Examples of the vinyl esters include vinyl acetate and vinyl propionate. Ester, vinyl butyrate, methoxy vinyl acetate, vinyl benzoate, etc. Examples of maleic acid diesters Examples thereof include dimethyl maleate, diethyl maleate, and dibutyl maleate. Examples of the fumaric acid diesters include antibutene Dimethyl methacrylate, diethyl fumarate, and dibutyl fumarate, etc. Examples of the homogenic acid diesters include dimethyl itaconate and diethyl itaconate. And -19- 200821362 dibutyl butylate, etc. Examples of (meth) acrylamides include (meth) acrylamide, N-methyl (meth) acrylamide, N-B. (meth) acrylamide, N-propyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-n-butyl (meth) acrylamide, N- Tributyl (meth) acrylamide, N-cyclohexyl (meth) acrylamide, N-(2-methoxyethyl) (meth) acrylamide, N, N-dimethyl ( Methyl) acrylamide, N,N-diethyl (meth) acrylamide, N-phenyl (meth) acrylamide, N-benzyl (meth) acrylamide, (methyl) Propylene porphyrin, diacetone acrylamide, and the like. Examples of the styrenes include styrene, methyl styrene, dimethyl styrene, trimethylstyrene, ethyl styrene, isopropyl styrene, butyl styrene, hydroxystyrene, and methoxy. Styrene, butoxy styrene, ethoxylated styrene, chlorostyrene, dichlorostyrene, bromostyrene, chloromethylstyrene, a group capable of being removed with an acidic substance (eg t- Boc (t-butyl 〇 Xycarbonyl; third butoxycarbonyl), etc.) protected hydroxystyrene, methyl benzoate, and α-methyl styrene. Examples of the vinyl ethers include methyl vinyl ether, butyl vinyl ether, hexyl vinyl ether, and methoxyethyl vinyl ether. The acid value of the specific pigment dispersant of the present invention is preferably 10 to 150 mg Κ 0 Η / g, more preferably 20 to 140 mg Κ 0 Η / gram, and particularly preferably 30 to 120 mg Κ 0 Η / gram. When the acid value of the specific pigment dispersant is in the range of 10 to 150 mg Κ0 Η /g, when the pigment dispersion composition of the present invention is used as a photoresist liquid, the alkali solubility of the photoresist liquid is maintained locally at -20-200821362, Achieving good developability while achieving excellent pigment dispersion stability. The means for maintaining the acid value of the specific pigment dispersant in an appropriate range as described above may be, for example, a means for causing a polymer constituting the specific pigment dispersant to contain a copolymer component having an acid group of 1% or more, or dispersing a specific pigment. The polymer of the agent is added with a means such as an acid anhydride by a polymer reaction. Here, the acid value of the specific pigment dispersant means the number of milligrams of potassium hydroxide necessary for neutralizing i grams of the pigment. The unit of the acid value is mg KOH / gram I valence is the solution of the sapling solution into the fr titration solution (for example, aqueous sodium oxychloride solution or aqueous potassium hydroxide solution) to obtain the neutralization point, which can reach the neutral point. The amount of alkali solution required is calculated. At the time of titration, the neutralization point is determined, for example, by titration using a titration indicator such as helium or by using an automatic potentiometric titration apparatus. A preferred embodiment of the specific pigment dispersant of the present invention may suitably be a copolymerized unit containing 2 to 50% by mass of the monomer represented by the above formula (1), and more preferably 10 to 90% by mass. a copolymerization unit of a polymerizable oligomer having an ethylenically unsaturated bond at the terminal, a idO mass% derived from a copolymerization unit of a monomer having an acid group, and a copolymerization ratio of from 20 to 20% by mass of a copolymerization unit derived from a vinyl monomer Things. The preferred molecular weight of the specific pigment dispersant of the present invention is preferably from 15,000 to 200,000 by weight average molecular weight (Mw), and preferably from 8,000 to 100,000 by number average molecular weight (Mn). Further, the molecular weight can be measured by gpc. Specific examples of the pigment dispersion agent which can be suitably used in the pigment dispersion composition of the present invention [exemplified compound 1 to exemplary compound 16] are the same as the weight average molecular weight thereof, but the present invention is not limited thereto. This is the case. Illustrative compound (1): the above-mentioned monomer M-2/terminal methacryl oxime polymethyl methacrylate copolymer (10/90% by mass, weight average molecular weight: 50,000, acid value: 0 mg KOH/g) Compound (2): the aforementioned monomer M-2/methacrylic acid/terminal methacryl oxime polymethyl methacrylate copolymer (10/15/75 mass%, weight average molecular weight: 30,000, acid value: 98 mg) KOH/g) ^ exemplified compound (3): the above-mentioned monomer M-3 / 2-hydroxyethyl methacrylate / terminal methacryl oxime polymethyl methacrylate copolymer (5/10/85 mass%, Weight average molecular weight: 40,000, acid value: 0 mg KOH / gram) Illustrative compound (4): the aforementioned monomer M-3 / methacrylic acid / benzyl methacrylate copolymer / terminal methacrylic acid polymethacrylic acid Methyl ester copolymer (15/5/10/65 mass%, weight average molecular weight: 60,000, acid value: 33 mg KOH/g) φ exemplified compound (5): the aforementioned monomer M-4/terminal methacrylic acid Polymethyl methacrylate copolymer (10/90% by mass, weight average molecular weight: 80,000, acid value: 0 mg KOH/g) exemplified compound ( 6): the above monomer M-4 / methacrylic acid / terminal methacrylic acid polymethyl methacrylate copolymer (1 0/1 5 / 7.5 mass%, weight average molecular weight of 30,000, acid value: 98 Mg KOH 7 g) exemplified compound (7): the aforementioned monomer M-5/acrylic acid/terminal methacryl oxime polymethyl methacrylate copolymer (25/1 5/60% by mass, weight average -22-200821362 The amount is 60000, acid value: 117 mg KOH/g. Illustrative compound (8): the above-mentioned monomer M-5/terminal methacryl oxime polybutyl methacrylate copolymer (15/85 mass%, weight average) Molecular enthalpy is 40,000, acid value: 〇mg KOH / gram) Illustrative compound (9): the aforementioned monomer M-6 / 2-hydroxyethyl methacrylate / terminal methacryl oxime polymethyl methacrylate copolymer (15/1 0/7 5 mass%, weight average molecular weight: 80000, acid value: 0 mg KOH/g) Illustrative compound (10): the aforementioned monomer M-6/terminal methacrylic acid poly(methacrylic acid) Methyl ester copolymer (12/88% by mass, weight average molecular weight: 50,000, acid value: 〇mg KOH/g) Illustrative compound (11): the aforementioned monomer M-7/methyl propyl Acid/terminal methacrylic acid polymethyl methacrylate copolymer (10/15/75 mass%, weight average molecular weight: 25000, acid value: 98 mg KOH/g) exemplified compound (12): the aforementioned monomer M -7/methacrylic acid/benzyl methacrylate/methoxy polyethylene glycol methacrylate copolymer (10/10/5 0/3 0 φ mass%, weight average molecular weight: 40,000, acid value: 65 MG KOH/g) Illustrative compound (13): the aforementioned monomer M-10/2-hydroxyethyl methacrylate/terminal methacryl oxime polystyrene copolymer (5/10/85 mass%, weight average molecular weight 20,000, acid value: 〇mg KOH/g) Illustrative compound (14): the aforementioned monomer M-10/methacrylic acid/terminal methacryl oxime polymethyl methacrylate copolymer (10/15/75 mass) %, weight average molecular weight: 35,000, acid value: 98 mg KOH/g) Illustrative compound (15): the aforementioned monomer M-10/methoxypolyethylene glycol methyl-23-200821362 acrylate copolymer (15/ 85 mass%, weight average molecular weight: 15000, acid value: 0 mgKOH/g) Illustrative compound (16): the aforementioned monomer M-13/methacrylic acid/ Methyl methacrylate deuterated polymethyl methacrylate copolymer (1 〇 / 1 5 / 7.5 % by mass, weight average molecular weight: 20,000, acid value: 98 mg KOH / gram) Illustrative compound (17): the aforementioned monomer M-4/methacrylic acid/terminal methacryl oxime polymethyl methacrylate copolymer (10/15/75 mass%, weight average molecular weight 25000, acid value: 98 mg KOH/g) exemplified compound (18) ): the aforementioned monomer M-4/acrylic acid/terminal methacrylic deuterated polystyrene copolymer (10/10/80% by mass, weight average molecular weight: 20,000, acid value: 78 mg KOH/g) exemplified compound (19) ): succinic anhydride adduct of the above-mentioned monomer M-4/methylpropionic acid 2-hydroxyethyl ester/terminal methacrylic acid polymethyl methacrylate copolymer (8/15/77 mass%, weight) The average molecular weight is 25,000, acid value: 37 mg KOH/g. Illustrative compound (20): the aforementioned monomer M-4/acrylic acid/benzyl methacrylate/terminal methacrylic acid polymethyl methacrylate copolymer ( 10/10/10/70% by mass, weight average molecular weight 25000, acid value: 78 mg KOH/g) Illustrative compound (21) ·· Monomer M-10/acrylic acid/terminal methacryl oxime polymethyl methacrylate copolymer (1 5 /1 0/7 5 mass%, weight average molecular weight 25000, acid value: 78 mg KOH/g) Compound (22): the aforementioned monomer M-11/methacrylic acid/terminal methyl-24 - 200821362 propylated polymethyl methacrylate copolymer (15/1 〇/75 mass%, weight average molecular weight 25,000) Acid value: 65 mg ΚΟΗ/g) Illustrative compound (23): the above-mentioned monomer Μ-11/terminal methacryl oxime polymethyl propyl methacrylate copolymer (15/85 mass%, weight average molecular weight is 30000, acid value: 〇mgΚΟΗ/g) The copolymer of the above-mentioned 'specific pigment dispersant, as described above, can be made by using the monomer represented by the above formula (1), if necessary, having low polymerizability The poly(monomer) or other monomer is obtained by radical polymerization in a solvent. As the radical polymerization initiator, a well-known compound can be used, and an azo initiator (for example, dimethyl-2,2'-azobis(2-methylpropionate), azobisindole isobutyronitrile, 2) can be suitably used. , 2'-azobis(2-methylamidinopropane) 2 hydrochloride, etc.), peroxide (benzaldehyde peroxide, potassium persulfate, etc.). It may also be synthesized by adding an initiator and further adding a chain transfer agent (e.g., 2-hydrothioethanol, 3 · thiopropylpropionic acid, 2-hydrothioacetic acid, dodecyl mercaptan). Further, a specific synthesis example will be described later. The content of the specific pigment dispersant in the pigment dispersion composition is preferably from 0.5 to 100% by mass, more preferably from 3 to 70% by mass, based on the mass of the pigment described later. When the amount of the pigment dispersant is within this range, a sufficient pigment dispersion effect can be obtained. Moreover, even if the amount of the pigment dispersant added is more than 100% by mass, it is not expected to further enhance the pigment dispersion effect. The pigment dispersion composition of the present invention contains a pigment and a specific pigment dispersant in an organic solvent, and can be formed by using other components such as a resin component as necessary. -25- 200821362 Since the pigment dispersion composition contains a specific pigment dispersant, the dispersion state of the pigment in the organic solvent becomes good, and good color characteristics can be obtained. At the same time, for example, a color filter can be obtained with high contrast. . In particular, it exhibits an excellent dispersion effect in an organic pigment. [Pigment] The pigment dispersion composition of the present invention contains a pigment, and the pigment can be used by appropriately selecting various inorganic pigments or organic pigments which have been conventionally known. Regardless of whether the pigment is an inorganic pigment or an organic pigment, it is preferable to use a particle size as small as possible in consideration of a high transmittance. When the handleability is also considered, the average particle diameter of the pigment is preferably from 1 μm to 0.1 μm, more preferably from 0.01 μm to 0.05 μm. The inorganic pigment may, for example, be a metal compound such as a metal oxide or a metal complex. Specific examples thereof include metal oxides such as iron 'cobalt, aluminum, cadmium, lead, copper, titanium 'magnesium, chromium, zinc, and antimony, and composite oxides of the above metals. The above organic pigment may, for example, be the following. CI·Pigment Yellow 11, 24, 31, 53, 83, 93, 99, 108, 109, 110, 138, 139, 147, 150, 15 154, 155 ^ 167, 180, 185, 199; CI Pigment Orange 36 , 38, 43, 71; CI Pigment Red 81, 1〇5, 122, 149, 150, 155, 171, 175, 176, 177, 209, 220, 224, 242, 254, 255, 264, 270; CI Pigment Violet 19, 23, 32, 37, 39; C · I · Pigment Blue 1, 2, 1 5, 1 5 ·· 1 , 1 5 ·· 3, 1 5 : 6, 1 6 , 2 2 , -26 - 200821362 60 ^ 66 ; CI Pigment Green 7, 36, 37; CI Pigment Brown 25, 28; CI Pigment Black 1, 7; The pigment of the present invention is not particularly limited, and the following pigments are preferred as CI Pigment Yellow 11, 24, 108 , 109, 110, 138, 139, 151, 154, 167, 180, 185; CI Pigment Orange 36, 71; • CI·Storage Red 122, 150, 17 1, 4 75, 177, 209, 22 4, 254 , 255 , 264 ; C. I. Pigment Violet 19, 2 3, 3 7 ; CI Pigment Blue 15 : 1, 15 : 3, 15 : 6, 16, 22, 60, CI Pigment Green 36 C. I. Pigment Black 7 Among these, the following pigments are particularly preferred. • CI Pigment Yellow 139, 150 C · I. Pigment Red 1 7 7 , 2 5 4 CI Pigment Violet 23 CI Pigment Blue 15 : 6 CI Pigment Green 36 These organic pigments can be used alone or in order to enhance color purity The way to use. Specific examples of the combination are shown in τ. For example, the red pigment can be used alone as an anthraquinone pigment, a phenanthrene 150, 242, 66; a pigment, a -27-200821362 diketopyrrolopyrrole pigment, or at least one of these and a bisazo system. A yellow pigment, an isoporphyrin yellow pigment, a quinoline yellow yellow pigment, or a mixture with a lanthanide red pigment. For example, the bismuth-based pigment may be CI Pigment Red 177, and the fluorene-based pigment may be C. I. Pigment Red 155, C. I. Pigment Red 2 24, Diketopyrrolopyrrole-based pigment It is preferable to mix CI Pigment Red 254 with CI Pigment Yellow 139 in terms of color reproducibility. Further, the mass ratio of the red pigment to the yellow pigment is preferably 100:5 to 00:50. When it is less than 1 〇〇 : 5 , it is difficult to suppress the light transmittance at 400 nm to 500 nm, and there is a case where the color purity cannot be improved. Further, when it is larger than 100:50, there is a case where the dominant wavelength is shifted to a short wavelength and the chromatic phase of the N T S C is largely deviated. In particular, the aforementioned mass ratio is preferably in the range of 100:10 to 00:30. Further, when the red pigments are combined with each other, they can be adjusted in accordance with the chromaticity. Further, the green pigment can be used alone as the halogenated indigo pigment, and it can also be used together with the disazo yellow pigment, the quinoline yellow pigment, the imine yellow pigment or the isoporphyrin yellow pigment. mixing. For example, such an example is mixed with CI·Pigment Green 7,36,37 with CI Pigment Yellow 83, CI Pigment Yellow 138, CI Pigment Yellow 139, C.I_Pigment Yellow 150, CI Pigment Yellow 180 or CI Pigment Yellow 185. It is better. The mass ratio of the green pigment to the yellow pigment is preferably 1 0 0 : 5 to 1 〇 〇 : 1 50 . When the mass ratio is less than 10 0 : 5 , it is difficult to suppress the light transmittance of 400 nm to 450 nm, and the color purity cannot be increased. Also, when it is greater than 1 00 : 1 50, the dominant wavelength is biased toward a long wavelength, which may greatly deviate from the NTSC standard hue. The mass ratio is particularly good in the range of 1 〇〇 : 30 to 100 · 120. -28- 200821362 Blue pigment can be used alone or in combination with a violet pigment. For example, it is preferred to mix C.I. Pigment Blue 15:6 with C.I. Pigment Violet 23. The mass ratio of the blue pigment to the purple pigment is preferably 100:0 to 100:50, more preferably 100:5 to 100:30. Further, the pigment for the black matrix may be a mixture of carbon, titanium black, iron oxide or titanium oxide alone or in combination, and a combination of carbon and titanium black is preferred. Further, the mass-to-weight ratio of carbon to titanium black is preferably in the range of 100 ° 〇 1 Q 〇 : 60. When it is greater than 1 0 0 : 6 0, there will be a situation in which the dispersion stability is low. The content of the pigment in the pigment dispersion composition is preferably 40 to 90% by mass, more preferably 50 to 8 % by mass, based on the total solid content (mass) of the composition. When the content of the pigment is within the above range, it is effective in ensuring excellent color characteristics due to sufficient color density. [Organic solvent] The organic solvent used for preparing the pigment dispersion composition of the present invention may, for example, be 2-ethoxycarbonyl-1-methoxypropane, 1-methoxy-2-propanol or ethylene glycol. φ methyl ether, diethylene glycol monomethyl ether, ethyl acetate, butyl acetate, ethyl lactate, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, n-propanol, 2- Propanol, n-butanol, cyclohexanol, ethylene glycol, diethylene glycol, toluene, xylene, and the like. Further, the amount of the organic solvent to be added can be appropriately selected depending on the use of the pigment dispersion composition and the like. However, when it is used to prepare a photocurable composition to be described later, the k-treatment property can be added so that the concentration of the solid content of the pigment and the pigment dispersant is 5 to 5 % by mass. -29- 200821362 The pigment dispersion composition of the present invention is prepared, and is not particularly limited. For example, a vertical or horizontal sand honing machine, a dial type mill, a slit mill, an ultrasonic disperser, or the like can be used. The beads, zirconia, or the like having a particle diameter of 0.01 to 1 mm are obtained by subjecting a pigment, a pigment dispersant, and a solvent to a fine dispersion treatment. Further, before the bead dispersion, two rolls, three rolls, a ball mill, a drum sieve mill, a disperser, a kneader, a kneading extruder, a homogenizer, a blender, and a single shaft can also be used. Or a twin-screw extruder or the like, and a kneading dispersion treatment is performed while imparting a strong shearing force. Further, the details of the kneading and dispersion are described in T.c. Patton, "Paint flow and Pigment Dispersion" (published by John Wiley and Sons, 1964). The pigment dispersion composition of the present invention can be applied to inkjet inkjet or the like in addition to the color filter. Further, when the pigment dispersion composition of the present invention is used for color filter formation, it is preferably soluble in an aqueous alkali solution. &lt;Photocurable composition&gt; The photocurable composition of the present invention contains the above-described pigment dispersion composition, photopolymer compound, and photopolymerization initiator of the present invention, and more preferably contains an alkali-soluble resin. It can contain other ingredients as necessary. Since the photocurable composition contains the specific pigment dispersant of the present invention described above, the pigment can maintain a good dispersion state in the composition, and can obtain good color characteristics from -30 to 200821362, and for example, when constituting a color filter. Can get high contrast at the same time. Hereinafter, each component contained in the photocurable composition of the present invention will be described in detail. [Pigment Dispersion Composition] The photocurable composition of the present invention is constituted by using at least one of the above-described pigment dispersion compositions of the present invention. Regarding the photocurable composition, the details of the pigment dispersion composition of the present invention are as described above. The content of the pigment dispersion composition in the photocurable composition of the present invention is preferably in the range of 5 to 70% by mass based on the total solid content (mass) of the photocurable composition. It is more preferably in the range of 15 to 60% by mass. When the content of the pigment dispersion composition is within this range, the color density is sufficient to effectively ensure excellent color characteristics. [Alkali-Soluble Resin] The photocurable composition of the present invention preferably contains at least one alkali-soluble tree φ lipid, and the photocurable composition is applied to the photocuring method by using a photolithography method by containing an alkali-soluble resin. When the composition forms a pattern, pattern formability can be improved. The alkali-soluble resin-based linear organic high molecular polymer can have at least one base which promotes alkali solubility (for example, a carboxyl group, a molecule (preferably an alkali copolymer or a styrene copolymer-based molecule). The alkali-soluble resin of a phosphate group, a sulfonic acid group, etc. is suitably selected. Among them, an alkali-soluble resin which is soluble in an organic solvent and can be developed by a weak alkali aqueous solution is more preferable. -31 - 200821362 For the production of an alkali-soluble resin, for example, a method by a well-known polymerization method can be applied. The polymerization conditions of the temperature, the pressure, the type and amount of the radical initiator, the kind of the solvent, and the like when the alkali-soluble resin is produced by the radical polymerization method can be easily set by the manufacturer, and can also be experimentally specified. The way to proceed. The linear organic high molecular polymer described above is preferably a polymer having a carboxylic acid in a side chain. For example, JP-A-59-446-15, Special Gong-zhao 54-34327, Special Gong-zhao 5 8- 1 2577, Special Gong-zhao 54-25957, and Special Kai-z 5 5-5 3 8 36, A methacrylic acid copolymer, an acrylic acid copolymer, an itaconic acid copolymer, a crotonic acid copolymer, a maleic acid copolymer, a partially esterified cis-butyl group described in each of the publications of JP-A-5-9-7 048 An enedic acid copolymer or the like, an acid cellulose derivative having a carboxylic acid in a side chain, a product obtained by adding an acid anhydride to a polymer having a hydroxyl group, and the like, and having a (meth) acrylonitrile group in a side chain. High molecular weight polymers are also preferred. Among these, a multicomponent copolymer composed of a benzyl (meth) acrylate/(meth)acrylic copolymer φ or a benzyl (meth) acrylate / (meth) acrylate / other monomer It is especially suitable. Further, a product obtained by copolymerizing 2-hydroxyethyl methacrylate or the like is also useful. The polymer can be used in any amount by mixing. In addition to the above, 2-hydroxypropyl (meth)acrylate/polystyrene macromonomer/methacrylic acid/benzyl methacrylate/methacrylic acid copolymer described in JP-A-H07-140654, 2 _Hydroxy-3-phenoxy propyl acrylate / polymethyl methacrylate huge monomer / benzyl methacrylate / methacrylic acid - 32 - 200821362 copolymer, 2-hydroxyethyl methacrylate / polystyrene A large monomer/methyl methacrylate/methacrylic acid copolymer, 2-hydroxyethyl methacrylate/polystyrene macromonomer/benzyl methacrylate/methacrylic acid copolymer, and the like. The specific structural unit of the alkali-soluble resin is particularly suitable as a copolymer of (meth)acrylic acid and the other monomer copolymerizable with it. The other monomer which can be copolymerized with (meth)acrylic acid may, for example, be an alkyl (meth)acrylate, an aryl (meth)acrylate or a vinyl compound. Here, the hydrogen atom of the alkyl group and the aryl group may also be substituted with a substituent. ^ Specific examples of the alkyl (meth)acrylate and the aryl (meth)acrylate include methyl (meth)acrylate, ethyl (meth)acrylate, and propyl (meth)acrylate. Butyl acrylate, isobutyl (meth)acrylate, amyl (meth)acrylate, hexyl (meth)acrylate, octyl (meth)acrylate, phenyl (meth)acrylate, benzyl acrylate , toluene acrylate, naphthalene acrylate, cyclohexyl acrylate, and the like. Further, examples of the vinyl compound include styrene, α-methylbenzene φ ethylene, vinyl toluene, glycidyl methacrylate, acrylonitrile, vinyl acetate, fluorene-vinylpyrrolidone, and A. Tetrahydrofurfuryl acrylate, polystyrene giant monomer, polymethyl methacrylate huge monomer, (: 仏 &lt;& 1 ft 2 [herein, R1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R2 represents an aromatic hydrocarbon ring having 6 to 10 carbon atoms], and CHarCUiKCOOR3) [here, R1 represents A hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R3 represents an alkyl group having a carbon number of i to 8 or an aralkyl group having a carbon number of 6 to 12 or the like. These other monomers which can be copolymerized can be used singly or in combination of two or more types from -33 to 200821362. Preferably, the other single system capable of copolymerization is selected from the group consisting of CHfCW, CHa^C^I^MCOOR3), phenyl (meth)acrylate, benzyl (meth)acrylate, and at least one of styrene, as CH^ CW, and/or (:^ = (:(111)((:〇〇113) is particularly preferred. These 111, 112, and 113 are each synonymous with the foregoing. Alkali-soluble resin in the photocurable composition The content is preferably from 1 to 20% by mass, more preferably from 2 to 15% by mass, even more preferably from 3 to 12% by mass, based on the total solid content of the composition. The photocurable composition of the present invention contains at least k of the photopolymerizable compound. The photopolymerizable compound which can be used in the present invention is an addition polymerizable compound having at least one ethylenically unsaturated double bond, and can be selected from A compound of at least one, preferably two or more terminally unsaturated bonds. Such a compound group is widely known in the industrial field, and in the present invention, φ is not particularly limited and can be used. For example, monomers, prepolymers, ie, dimers, trimers, and low The chemical form of the substance, or a mixture thereof, and copolymers thereof, etc. The monomer and the copolymer thereof may, for example, be an unsaturated carboxylic acid (for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, or the like). Crotonic acid, maleic acid, etc., or esters thereof, guanamines, using an ester of an unsaturated carboxylic acid and an aliphatic polyol compound, an amide of an unsaturated carboxylic acid and an aliphatic polyamine compound, Further, an unsaturated carboxylic acid ester or decylamine having a nucleophilic substituent such as a hydroxyl group, an amine group or a thiol group, and a mono-functional energy-34-200821362 or a polyfunctional isocyanate or an epoxy compound The reactants and the dehydration condensation reaction with a monofunctional or polyfunctional carboxylic acid are also suitably used. Further, an isocyanate group or an unsaturated carboxylic acid ester or guanamine having an electrophilic substituent such as an epoxy group and a single An addition reaction of a functional or polyfunctional alcohol, an amine or a thiol, and an unsaturated carboxylic acid ester or decylamine having a detachable substituent such as a halogen group or a p-toluenesulfonyloxy group; Monofunctional or polyfunctional alcohols, amines, thiols The reactants are also suitable. Further, other examples can also be used in place of the above unsaturated carboxylic acid in the group of compounds which have been substituted with unsaturated phosphonic acid, styrene, vinyl ether, etc. Aliphatic polyol compounds and unsaturated groups Specific examples of the monomer of the carboxylic acid ester include ethylene glycol diacrylate, triethylene glycol diacrylate, 1,3-butylene glycol diacrylate, butanediol diacrylate, and propylene glycol diacrylic acid. Ester, neopentyl glycol diacrylate, trimethylolpropane triacrylate, trimethylolpropane ginseng (propylene oxypropyl) ether, trimethylolethane triacrylate, hexanediol diacrylate Ester, 1,4-cyclohexanediol diacrylate, φ tetraethylene glycol diacrylate, neopentyl alcohol diacrylate, neopentyl alcohol triacrylate, neopentyl alcohol tetraacrylate, dioxane Tetraol diacrylate, dipentaerythritol hexaacrylate, sorbitol triacrylate, sorbitol tetraacrylate, sorbitol pentaacrylate, sorbitol hexaacrylate, ginseng Trimeric isocyanate, polyester Acrylate oligomer, isocyanuric acid EO-modified triacrylate. Methacrylates are butanediol dimethacrylate, triethylene glycol dimethacrylate, neopentyl glycol dimethacrylate, trimethylolpropane tri-35- 200821362 methacrylate, three Hydroxymethylethane trimethacrylate, ethylene glycol dimethacrylate, 1,3-butanediol dimethacrylate, hexanediol dimethacrylate, neopentyl alcohol dimethacrylate Ester, neopentyl alcohol trimethacrylate, neopentyl alcohol tetramethacrylate, dipentaerythritol dimethacrylate, dipentaerythritol hexamethacrylate, sorbitol trimethyl Acrylate, sorbitol tetramethacrylate, bis[p-(3-methylpropenyloxy-2-hydroxypropoxy)phenyl]dimethylmethane, bis-[p-_(methacryl)醯oxyethoxy)phenyl]dimethylformamidine and the like. Iconic acid esters include ethylene glycol diconconate, propylene glycol diconcanate, 1,3-butanediol diconconate, iota, 4-butanediol diconconate, and dibutyl Alcohol-Iconate, neopentyl alcohol diconconate, sorbitol tetraconate, and the like. The crotonate is ethylene glycol dicrotonate, butanediol dicrotonate, pentaerythritol dicrotonate, sorbitol tetradodetoic acid ester, and the like. The isocrotonate includes ethylene glycol diisocrotonate, pentaerythritol diisocrotonate, and sorbitol tetraisocrotonate. Maleic acid esters include ethylene glycol dimaleate, triethylene glycol dimaleate, pentaerythritol di maleate, sorbitol tetramaleic acid Ester and the like. Examples of the other esters include, for example, the aliphatic alcohol-based esters described in Japanese Patent Publication No. Sho. No. Sho. No. Sho 57-34, No. 57-1536, or JP-A-59-9-5240, JP-A-59-5241 The aromatic skeleton described in JP-A-2-226149, and the amine group-containing product described in JP-A No. 1 -1 65 6 1 3 are also suitably used. Further, the aforementioned ester monomers may also be used in the form of a mixture. Further, a monomer of an aliphatic polyamine compound and an amine of an unsaturated carboxylic acid has a composition of methylene bis-acrylamide, methylene bis-methyl decylamine, 1,6- Hexamethylene bis-acrylamide, hydrazine, 6-hexamethylene bis-methyl acrylamide, di-ethyltriamine propylene amide, benzodimethyl bis decylamine, benzene dimethyl Dimethacrylamide and the like. Other examples of the preferred amide-based monomer include those having a cyclohexene structure as described in Japanese Patent Publication No. Sho 54-2 1726. Further, it is also preferable to use an amino acid-based ester-addition polymerizable compound produced by an addition reaction of an isocyanate and a hydroxyl group, and a specific example thereof is described in JP-A-48-41708, which is described in JP-A-48-41708. In the polyisocyanate compound having two or more isocyanate groups, a vinyl group containing a hydroxyl group represented by the following formula (A) is added, and a vinylamine having two or more polymerizable vinyl groups in one molecule is added. Carbamate compound, etc. CH2, two C(R34)C〇〇CH2CH(R35)〇H (A) (wherein R34 and R35 are Η or CH3), and have the same as that of the special opening 5 1 - 3 7 1 9 3 - 3 2 2 9 No. 3, Special # Fair 2 - No. 6765, the urethane amides, or the special public, No. Sho 58-498 No. 60, 'Special Gong Zhao 5 6- 1 7654, Special Gong Zhao 62-394 1 The urethane-based urethane compound described in No. 7 and JP-A-62-3394 is also preferred. Further, an amine group structure or a thioether is contained in the molecule as described in JP-A-63-237, No. 63-260909, JP-A No. Hei No. Hei. The addition polymerizable compound of the structure can obtain a photopolymerizable composition having a very excellent photospeed. Other examples include polyester-type acrylic acid described in each of the publications, such as Japanese Patent Publication No. 4-8-6 4 1 8 3, Japanese Patent Publication No. SHO-37-200821362, No. 49-43, No. A polyfunctional acrylate or methacrylate such as an epoxy acrylate obtained by reacting an ester or an epoxy resin with (meth)acrylic acid. In addition, a specific unsaturated compound described in Japanese Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. A compound or the like. Further, in some cases, the structure containing a perfluoroalkyl group described in JP-A-61-250 is also suitable for use. Further, it can also be used as a photocurable monomer and an oligomer as described in Japanese Journal of the Association, Vol. 20, No. 7, pp. 300-308 (1 984). The details of the methods of use, such as the structure, the individual use, the use, and the amount of addition, of the addition polymerizable compound can be arbitrarily set in accordance with the performance design of the final photocurable composition. For example, it can be selected from the following points of view. In terms of sensitivity, a structure having a large content of unsaturated groups per molecule is preferably φ, and most of the cases are preferably two or more. Further, in order to increase the strength of the cured film, it is preferably a trifunctional or higher functional group, and a different functional group or a different polymerizable group (for example, an acrylate, a methacrylate, a styrene compound, or a vinyl ether compound) is used. The method of adjusting the sensitivity and intensity is also effective. Further, the compatibility and dispersibility of other components in the photocurable composition (for example, a binder polymer such as an alkali-soluble resin, a photopolymerization initiator, and a colorant (pigment)), and the addition of an addition polymerization compound The use of the law is heavy -38- 200821362. For example, by using a low-purity addition polymerization compound or by using two or more addition polymerization compounds, compatibility with other components can be improved. % Further, the selection of a specific structure can also improve the adhesion to a substrate or the like. The addition polymerizable compound is preferably 5 to 70% by mass, more preferably 10 to 60% by mass, based on the nonvolatile component in the photocurable composition. Further, these can be used alone or in combination of two or more. In addition, from the viewpoints of the inhibition of the polymerization of oxygen, the size, the resolution, the fog, the refractive index, the surface adhesion, and the like, the method of using the addition polymerizable compound can arbitrarily select an appropriate structure, blending, The amount added. [Photopolymerization Initiator] The photocurable composition of the present invention contains at least one of polymerization initiators. The photopolymerization initiator is described in, for example, the halomethyl fluorene diazole described in JP-A-57-6096, JP-A-59-128, and JP-A-53-133 An active halogen compound such as a halomethyl-s-three-till, a ketal, an acetal or a benzoin alkyl group as described in the specification of the US Patent No. USP-43 1 879 1 and European Patent Publication EP-8 805 0A. An aromatic carbonyl compound such as an ether, an aromatic ketone compound such as a diphenyl ketone described in the specification of US Pat. No. 4,199420, and a (thio)xanthone ((Thio) described in the specification of Fr-245 674 1 x 特 8 8 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 -0 Organic boron complexes and the like. In particular, the photopolymerization initiator of the photocurable composition of the present invention contains -39-200821362, which is selected from the group consisting of an acetophenone compound, a ketal compound, a diphenyl ketone compound, a benzoin compound, and benzene. A formamidine compound, a xanthone compound, a triple well compound, a halomethyl fluorene diazole compound, an acridine compound, a coumarin compound, a spheroid dimer compound, and a diimidazole A photopolymerization initiator such as a compound or a ruthenium compound is more preferable, and a photopolymerization initiator containing a compound selected from the group consisting of a tritrap compound, a spheroid dimer compound, and an anthracene compound is particularly preferable. The photopolymerization initiator of the above acetophenone type may suitably be, for example, 2,2-diethoxyethyl benzene, p-dimethylamino acetophenone or 2-hydroxy-2-methyl-1 phenyl phenyl group. - propan-1-one, p-dimethylaminoethyl benzene, 4'-isopropyl-2-hydroxy-2-methyl-propenyl benzene, and the like. The ketal-based photopolymerization initiator may, for example, be benzyl dimethyl ketal, benzyl-/3-methoxyethyl condensate or the like. The diphenylketone-based photopolymerization initiator may suitably be, for example, diphenyl ketone, 4,4'-(bisdimethylamino)diphenyl ketone, 4,4'-(bisdiethylamine). Diphenyl ketone, 4,4'-dichlorodiphenyl ketone, 1-hydroxy-cyclohexyl-phenyl-one, 2-benzyl-2-dimethylamino-1-(4-carboline Phenyl)-butanone-1, 2-tolyl-2-dimethylamino-1-(4-morpholinylphenyl)-butanone-1, 2-methyl-1-[4-(methyl sulfide Base) phenyl]_ 2 - sulphonic acid acetone-1 and the like. The benzoin-based compound or the benzamidine-based photopolymerization initiator may suitably be, for example, benzoin isopropyl ether, benzoin isobutyl ether, benzoin methyl ether, ortho-benzoylbenzene. Methyl formate and the like. The xanthone-based photopolymerization initiator may suitably be exemplified by the example-40-200821362 such as diethyl thiaxanthone, diisopropylthiaxanthone, monoisopropylthiazinone, Chlorothidone ketone and the like. The photopolymerization initiator of the above-mentioned three tillage system may suitably be, for example, 2,4-bis(trichloromethyl)-6-p-methoxyphenyl tritonate or 2,4-bis(trichloromethyl)-6. -p-methoxystyryl-s-trin, 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3-butadienyl-s -Tri-trap, 2,4-bis(trichloromethyl)-6-biphenyl-s-tripper, 2,4-bis(trichloromethyl)-6-(p-methylbiphenyl)- S-tripper, p-hydroxyethoxystyryl-2,6-di(trichloromethyl)-s-trin, methoxystyryl-2,6-di(trichloromethyl)- 8-three tillage '3,4-dimethoxystyryl-2,6-di(trichloromethyl)-8-triazine, 4-benzoxoxycyclopentane-2,6-di (three Chloromethyl)-5-three tillage, 4-(o-bromo-p-anthracene, fluorenyl-(diethoxycarbonylamino)-phenyl)-2,6-di(chloromethyl)-s- Three tillage, 4-(p-indene, indole-(diethoxycarbonylaminophenyl)-2,6-di(chloromethyl)-s-three tillage, etc. The aforementioned halomethyl oxadiazole series The photopolymerization initiator may suitably be, for example, 2-trichloromethyl-5-styryl-1,3,4-oxadiazole or 2-trichloromethyl-5-(cyanoφstyryl)- 1,3,4-oxadiazole, 2-three Methyl-5-(naphthalene-buyl)-1,3,4-oxadiazole, 2-trichloromethyl-5-(4-styryl)styryl-1,3,4-anthracene The acridine-based photopolymerization initiator may, for example, be 9-phenyl acridine or 1,7-bis(9-acridinyl)heptane. The photopolymerization of the aforementioned coumarins is preferred. The initiator may suitably be, for example, 3-methyl-5-amino-((s-trit-2-yl)amino)-3-phenylcoumarin, 3-chloro-5-diethylamino -((s-trit-2-yl)amino)-3-phenylcoumarin, 3-butyl-5-dimethylamine-41- 200821362 ke-((s-tris-2-yl) Amino) 3-phenyl coumarin, etc. The photopolymerization initiator of the above-mentioned spheroid dimer type may suitably be, for example, 2-(o-chlorophenyl)-4,5-diphenylimidazolyl Polymer, 2-(o-methoxyphenyl)-4,5.diphenylimidazolyl dimer, 2-(2,4-dimethoxyphenyl 4,5-diphenylimidazolyl dimerization The diimidazole-based photopolymerization initiator may, for example, be 2-hydroxythiobenzimidazole or 2,2'-benzothiazolyl disulfide. The above-mentioned fluorene-based photopolymerization initiator may be mentioned. For example, 丨-phenylpropanedione-2-(o-ethoxycarbonyl)肟, o-benzhydryl _4' _(benzohydrothio) benzhydryl-hexyl-ketone oxime, and, by way of example, LC.S. Perkin II (197 9) 1 65 3- 1 660 pages), JLC.S. Perkin II (1 979) pp. 156-162, J ournal of Photopolymer Science and Technology (195), pp. 202-232 The compounds described in JP-A-2000-86385, JP-A-2000-80068, and JP-A-2004-534797. The photopolymerization initiator other than the above may, for example, be a 2,4,6-trimethylphenylcarbonyl-diphenylphosphonium ruthenium oxide or a hexafluorophosphono-trialkylphenyl iron salt. The photopolymerization initiator which can be used in the present invention is not limited to the above-mentioned photopolymerization initiator, and other known materials can be used. For example, the vicinal polyketal aldehyde compound described in the specification of U.S. Patent No. 2,367,660, the α-carbonyl compound described in the specification of U.S. Patent Nos. 2,367,661 and 2,367,670, and the specification of U.S. Patent No. 2,448,828. The acyloin ether described in the acyloin ether, and the aromatic acyloin compound substituted by an α-hydrocarbon described in the specification of the Japanese Patent No. 2,722,512, and the US Patent No. 3, 美国Combination of the polynuclear compound described in the specification of No. 46,127 and No. 2,951,7,58, and the combination of triallyl imidazole dimer/p-aminophenyl ketone described in the specification of U.S. Patent No. 3,549,357, The benzothiazole-based compound/trihalomethyl-S-tripleenic compound described in the publication No. 5 1 - 4 8 5 1 6 . Further, such photopolymerization initiators can also be used. The content of the photopolymerization initiator in the photocurable composition is preferably from 0.1 to 15.0% by mass, more preferably from 0.5 to 10.0% by mass, based on the total solid content of the composition. When the content of the photopolymerization initiator is within this range, the polymerization reaction can be favorably carried out to form a film having good strength. The photocurable composition of the present invention may contain a sensitizer for the purpose of increasing the radical generating efficiency of the photopolymerization initiator (radical initiator) and increasing the wavelength of the photosensitive wavelength. The ancillating agent which can be used in the present invention is preferably one which is capable of increasing the sensitivity of the radical initiator by an electron-moving mechanism or an energy-moving mechanism. The sensitizer which can be used in the present invention is exemplified by the following compounds, and has an absorption wavelength in a wavelength region of from 300 nm to 450 nm. Examples of preferred sensitizers include those belonging to the following compounds and having an absorption wavelength in a wavelength region of from 3,000 nm to 45 nm. For example, polynuclear aromatics (such as 'phenanthrene, anthracene, anthracene, anthracene, tnphenylene, 9,10-dialkoxyfluorene), xanthene (for example, luciferin, blush, red fluorescein) , Rhodamine B, rose red), exposure (isopropyl _ -43- 200821362 xanthone, diethyl thiaxanthone, chlorthathiamone), anthocyanins (such as thiophene) Carbonic cyanine, anthocyanin), anthocyanins (such as merocyanine, carbonaceous anthocyanins), indigo, thiamat (such as sulfur, methylene blue, toluidine blue), 吖Pyridines (eg, acridine orange, chlorsulfurin, acriflavine), terpenoids (eg, sputum), snail key (eg, snail key), acridine orange, coumarin (eg, two) Ethylamino-4-methylcoumarin), ketocoumarin, thioanthin, morphine, styrylbenzene, azo compound, diphenylmethane, triphenylmethane, stilbene Benzene, carbazole, laverine, spiro compound, quinophthalone, indigo, styrene, pyridyl compound, methylpyrrole compound, pyrazole triazole compound, benzothiazole compound, barbitic acid Derivatives, thiobarbituric acid derivatives, acetophenone, diphenyl ketones, thioxanthone, aromatic ketone compounds such as Michelin, and heterocyclic compounds such as N-aryl oxazolidinone . The photocurable composition of the present invention preferably contains a co-sensitizer. The co-sensitizer of the photocurable composition of the present invention has an effect of increasing the sensitivity of the sensitizing colorant or the initiator to the actinic radiation, or suppressing the φ polymerization inhibition of the polymerizable compound by oxygen. Such a co-sensitizer may, for example, be an amine, for example, MR Sander, etc. "Journal of Polymer Society", Vol. 10, p. 3173 (1 972), Te Gongzhao 44-20 1 89 Japanese Unexamined Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. The compound described in Research Disclosure No. 3 3 825, and the like, specifically, triethanolamine, p-44-200821362 dimethylaminobenzoic acid Ethyl ester, p-mercaptodimethylaniline, p-methylthiodimethylaniline, and the like. The other examples of the co-sensitizers are thiols and thioethers, and are described in, for example, JP-A-53-702, JP-A-55-5-1A, and JP-A-5-42772. The thiol compound, the disulfide compound of JP-A-5-6-7 643, and the like, specifically, 2-hydrothiobenzothiazepine, 2-hydrothiobenzoxanthene, 2- Hydrogenthiobenzimidazole, 2-hydrothio-4(3H)-quinazoline, anthracene-hydrothionaphthalene, and the like. Further, the other examples include an amino acid compound (for example, N-phenylglycine), an organometallic compound (for example, tributyltin acetate) described in Japanese Patent Publication No. Sho 48-42965, and a special public 55- A hydrogen donor according to the publication No. 344, No. 6-308727, for example, a sulfur compound (for example, trithiane) or the like. From the viewpoint of improving the curing rate by the balance between the polymerization growth rate and the chain transfer, the content of the total sensitizer such as φ is in the range of 0.1 to 30% by mass based on the mass of the total solid content of the photocurable composition. Preferably, it is preferably in the range of 1 to 25% by mass, more preferably in the range of 0.5 to 20% by mass. Next, components other than the above will be described. [Solvent] The photocurable composition of the present invention can be suitably prepared by using a solvent together with the above components. Examples of the ester of the solvent include ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl-45-200821362 ester, and isopropyl butyrate. Ester, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, Ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, and methyl 3-methoxypropionate and ethyl 3-oxypropionate Alkyl oxypropionates (for example, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate And an alkyl 2-oxopropionate such as methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate (for example, 2-methoxypropanoic acid) Methyl ester, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate 2-oxy-2- Methyl methacrylate, ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy-2-methylpropionate, 2-ethoxy-2-methylpropionic acid ethyl ester), and methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetate, ethyl acetate, 2-oxo oxime Methyl ester, ethyl 2-oxo decanoate, etc.; examples of the ethers include diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol mono φ methyl ether, ethylene glycol monoethyl ether, methyl赛路苏acetate, ethyl serosuacetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether acetate In the present specification, it is also referred to as 2-acetoxy-1-methoxypropane, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, etc.; The ketone, cyclohexanone, 2-heptanone, 3-heptanone, etc.; and aromatic hydrocarbons, for example, toluene, xylene, etc. are mentioned. -46 - 200821362 Among these, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl celecoxicillin, ethyl lactate, diethylene glycol dimethyl Ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether acetate Ester and the like are preferred. The solvent may be used singly or in combination of two or more. [Other components] The photocurable composition of the present invention can contain a fluorine-based organic compound, a thermal polymerization inhibitor, a dip material, a specific pigment dispersant, and a polymer compound other than the alkali-soluble resin, a surfactant, and a surfactant, if necessary. Adhere to various additives such as accelerators, antioxidants, UV absorbers, and anti-agglomerants. &lt;Fluorine-based organic compound&gt; By containing a fluorine-based organic compound, it is possible to improve the liquid properties (especially fluidity) when the coating liquid is used, and it is possible to improve the uniformity of the coating thickness or the liquid repellency. In other words, the interface between the substrate and the coating liquid is lowered to improve the wettability of the substrate, and the coating property to the substrate is improved. Therefore, even when a small amount of liquid is used to form a film of several micrometers or so, It is effective to form a film having a uniform thickness having a small thickness unevenness. The content of the fluorine-based organic compound is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass. When the fluorine content is in this range, it is effective in coating thickness uniformity or liquid-saving property, and the solubility in the composition is also good. Examples of the fluorine-based organic compound include MEGAFAC F171, F172, -47-200821362, F173, F177, F141, F142, F143, F144, R30, and F437 (above, Dainippon Ink Chemical Industry ( Stock)), FRORAD FC430, FC431, FC17U and above, Sumitomo 3M (share) system, SAFRON S-382, same SC-101, same SC-103, same SC-104, same SC-105, same SC 1068, the same as SC-381, the same SC- 3 8 3, the same as S 3 93, the same KH-4 〇 (above, Asahi Glass Co., Ltd.) _ ° Especially when the coating film formed by coating is thinned, 'fluorine system The organic compound is effective for preventing coating unevenness or thickness unevenness. Further, it is also effective in the application of slit coating which is liable to cause liquid shortage. The amount of the fluorine-based organic compound added is preferably 0.001 to 2.0% by mass, more preferably 0.005 to 1.0% by mass, based on the total mass of the pigment dispersion composition or the photocurable composition. &lt;Thermal polymerization initiator&gt; The photocurable composition of the present invention is also effective in containing a thermal polymerization initiator. Examples of the thermal polymerization initiator include various azo-based compounds and peroxy φ compound-based compounds, and examples of the azo-based compound include azobis compounds, and examples of the peroxide-based compounds include ketone peroxide and peroxidation. A ketal, hydrogen peroxide, a dialkyl peroxide, a ruthenium peroxide, a peroxyester, a peroxydicarbonate or the like. &lt;Intermediate Active Agent&gt; The photocurable composition of the present invention is preferably composed of various surfactants, and various non-ionic, cationic or anionic surfactants can be used. Among them, a fluorine-based surfactant having a nonionic interface -48-200821362 active agent and having a perfluoroalkyl group is preferred. Specific examples of the fluorine-based surfactant include, for example, the MEGAFAC (registered trademark) series manufactured by Dainippon Ink and Chemicals Co., Ltd., and the FLORAD (registered trademark) system manufactured by 3M Corporation. In addition to the above, specific examples of the additive in the photocurable composition include a coating material such as glass or alumina; an itaconic acid copolymer, a crotonic acid copolymer, a maleic acid copolymer, and a partially esterified cis. An alkali-soluble resin such as an enedic acid copolymer, an acidic cellulose derivative, a compound obtained by adding a hydroxyl group-forming acid anhydride, an alcohol-soluble nylon, a phenoxy resin formed of bisphenol A and epichlorohydrin; An interfacial activator such as an ion system, a cationic system, or an anionic system, and specifically an indigo derivative (commercial product No. 1^8-745 (manufactured by Morishita Sangyo Co., Ltd.)); an organic siloxane polymer KP341 (Shin-Etsu Chemical Industry) Company-made), (meth)acrylic (co)polymers POLYFRO No.75, No.90, No.95 (manufactured by Kyoeisha Oil Chemical Industry Co., Ltd.), W001 (made by Yusho Co., Ltd.) and other cationic surfactants φ Other additives and the like may, for example, be polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oil decyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene nonyl phenyl ether , polyethylene glycol dilaurate, polyethylene glycol two hard Acid esters, sorbitan fatty acid esters (PLURONIC L 1 0, L31, L61, L6 2, l〇R5, 17R2, 25R2, TETRONIC 304, 701, 7 04, 901, 904, 150R1, etc., manufactured by BASF Ionic surfactant; W004, W005, W017 (made by Yusho Co., Ltd.) and other anionic surfactants; EFKA-46, EFKA-47, EFKA-47EA, EFKA POLYMER 100, -49- 200821362 EFKA POLYMER400, EFKA POLYMER401, Polymer dispersant such as EFKA POLYMER450 (manufactured by Morishita Industrial Co., Ltd.), DISPERSAID6, DISPERSAID8, DISPERSAID15, DISPERSAID9100 (manufactured by SANNOPCO); SOLUSPAS 3000 &gt; 5000, 9000, 12000, 13240, 13940, 17000, 24000, 26000, 28000, etc. Various SOLUSPAS dispersions (made by ZENECA); ADEKAPLURONIC L31, F38, L42, L44, L61, L64, F68, L7 2, P95, F7 7, P84, F87, P94, L101, P103, F108, L121, P- 123 (made by Asahi Kasei Co., Ltd.) and ISONET S-20 (made by Sanyo Chemical Co., Ltd.); 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, alkane Ultraviolet absorber such as oxydiphenyl ketone; and polyacrylic acid Anti-agglomerating agent such as sodium. In addition, in order to promote the alkali solubility of the uncured portion and to improve the developability of the photocurable composition, it is possible to add an organic carboxylic acid to the photocurable composition, preferably a low molecular weight organic carboxylic acid having a molecular weight of 1,000 or less. acid. Specific examples thereof include aliphatic monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trimethyl phthalyl acetic acid, caproic acid, diethyl acetic acid, heptanoic acid, and octanoic acid; oxalic acid and malonic acid; , succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, tridecanedioic acid, methylmalonic acid, ethylmalonic acid, dimethyl propyl An aliphatic dicarboxylic acid such as diacid, methyl succinic acid, tetramethyl succinic acid or citraconic acid; an aliphatic tricarboxylic acid such as 1,2,3-propanetricarboxylic acid, aconitic acid or camphor tricarboxylic acid; , aromatic carboxylic acid such as phenylacetic acid, acrylic acid, diconic acid, 3,5-dimethylbenzoic acid; citric acid, isophthalic acid, citric acid, trimellitic acid, trimesic acid, partial Aromatic polycarboxylic acid such as pyromellitic acid, pyromoric acid-50-200821362; phenylacetic acid, hydrogen atoic acid, hydrogen cinnamic acid, mandelic acid, phenylsuccinic acid, atopic acid, cinnamic acid, cinnamic acid Other carboxylic acids such as methyl ester, benzyl cinnamate, cinnamic acid, coumaric acid, and valeric acid. (Prevention of Thermal Polymerization Agent) In the photocurable composition of the present invention, it is preferred to further contain a thermal polymerization preventing agent such as hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, gallic phenol, Third butyl catechol, benzoquinone, 4,4'-thiobis(3-methyl-6-_t-butylphenol), 2,2'-methylenebis(4-methyl- 6. Tributyl phenol), 2-hydrothiobenzimidazole, and the like are useful. The photocurable composition of the present invention can contain (preferably, together with a solvent) an alkali-soluble resin, a photopolymerizable compound, and a photopolymerization initiator in the pigment dispersion composition of the present invention, and if necessary, a mixed interface It is prepared by additives such as an active agent. &lt;Color filter and method for producing the same&gt; The color filter of the present invention is produced by forming a colored film (colored pattern) on a substrate such as glass by using the above-described photohardenable composition of the present invention. . Specifically, the photocurable composition of the present invention is applied directly or through another layer (preferably coated by a coating method such as spin coating, slit coating, cast coating, roll coating, etc.) on the substrate. A photosensitive film is formed. Exposing a predetermined mask pattern to the formed photosensitive film, and removing the uncured portion by using a developing solution after exposure to form a colored pattern (for example, a colored pixel) of each color (for example, three colors or four colors). Can produce the best color filter -51- 200821362 light film. According to this, it is possible to manufacture a color filter for a liquid crystal display element or a solid-state image sensor with less difficulty in manufacturing, high quality, and low cost. In this case, the radiation used for exposure is g-ray, h-ray, or Ultraviolet rays such as 1 ray and j ray are particularly preferable. A film formed of the photocurable composition of the present invention (preferably coated) on a substrate, which can be dried (prebaked) using a heating plate, an oven or the like to a temperature range of 50 ° C to 140 ° C It is carried out under the conditions of 10 seconds to 300 seconds. Development causes the unhardened portion after exposure to be eluted to the developer solution, and only the hardened portion remains. The development temperature is usually from 20 ° C to 30 ° C, and the development time is from 20 seconds to 90 seconds. Any developer can be used if it is a film which can be dissolved in the photocurable composition of the uncured portion and does not dissolve the hardened portion. A combination of various organic solvents or an aqueous alkaline solution can be used. φ The above-mentioned organic solvent or solvent which can be used in the preparation of the pigment dispersion composition or the photocurable composition of the present invention is exemplified. The alkaline aqueous solution may, for example, be sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium citrate, sodium metasilicate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine or hydrogen hydroxide. Basic compounds such as methylammonium, tetraethylammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo-[5,4,0]-7-undecene at a concentration of 0 · 00 1 to 10% by mass, preferably 〇· 〇1 to 1% by mass of -52 - 200821362 Formulated aqueous solution. Further, when an alkaline aqueous solution is used as a developing solution, it is usually washed (rinsed) with water after development. After the development, the remaining developer is removed by washing, and after drying, it is usually subjected to heat treatment (post-baking) at a temperature of from 100 ° C to 240 ° C. The post-baking is used to heat the hardened film after development, and is usually heated (hardened baking) at about 200 ° C to 250 ° C. This post-baking treatment can be carried out by a continuous or batch type using a heating means such as a hot plate or a convection oven (hot air circulation dryer) or a high frequency heating machine under the above conditions. By repeating the number of hue required for the above operation in accordance with the order of the respective colors, it is possible to manufacture a color filter formed by forming a cured film (a plurality of colors are colored). When the photocurable composition of the present invention is applied to a substrate to form a film, the film has a dry thickness of usually 0.3 μm to 5.0 μm, preferably 0.5 μm to 3.5 μm, and preferably 1.0 μm to 2.5 μm. Examples of the φ substrate include an alkali-free glass, a soda-lime glass, a PYREX (registered trademark) glass, a quartz glass, and a transparent conductive film adhered thereto, or a solid. A photoelectric conversion element substrate used for an image sensor or the like, for example, a germanium substrate or the like, and a plastic substrate. On these substrates, black stripes are typically formed to isolate the pixels. In the plastic substrate, it is preferred that the surface has a gas barrier layer and/or a solvent resistant layer. When a photocurable composition is provided by passing another layer on the substrate, the other layer of -53-200821362 may be a gas barrier layer or a solvent resistant layer. The above mainly describes the use of the pigment dispersion composition and the photocurable composition of the present invention centering on the use of the color filter, but can also be applied to form a black matrix for isolating the respective colored pixels constituting the color filter. . The black matrix can be subjected to pattern exposure, development, and post-baking as necessary by using a photocurable composition (pigment dispersion composition) of the present invention using a black pigment such as carbon black or titanium black as a pigment. Promotes the hardening of the film to form. [Examples] Hereinafter, the present invention will be more specifically described by the examples, but the present invention is not limited to the following examples without departing from the spirit of the invention. In addition, "parts" means "parts by mass" without prior notice. [Synthesis Example 1] (Synthesis of Monomer-1) 9.5 1 part of 2-aminopyrimidine was dissolved in 30 parts of pyridine and heated to φ 45 °C. On the other hand, 17.1 parts of ethyl 2-methylpropenyloxy isocyanate was added dropwise, and the mixture was further stirred under heating at 50 ° C for 5 hours. While stirring the reaction liquid, 200 parts of distilled water was poured, and the obtained precipitate was separated by filtration and washed to obtain 23.8 parts of monomer 1 (exemplified compound 2 described above). (Synthesis of Polymer 1) 5.0 parts of the above-mentioned monomers and 37.5 parts of polymethyl methacrylate (AA-6: manufactured by Toagosei Co., Ltd.) having methacryl oxime group at the terminal, 7.5 parts of methacrylic acid, and 116.7 parts of 1-methoxy-2-propanol was introduced into a three-necked flask, which was replaced with nitrogen, and stirred with a stirrer (Nippon Science Co., Ltd.: THREE ONE MOTOR) while allowing nitrogen gas to flow into the flask. The mouth heat is raised to 78 °C. To this was added 0.1 part of dimethyl-2,2'-azobis(2-propionic acid methyl ester) ("V-601" manufactured by Wako Pure Chemical Industries, Ltd.), and the mixture was stirred under heating at 78 t for 2 hours. After 2 hours, 1 part of V-601 was further added and stirred under heating for 3 hours to obtain a 30% solution of the polymer 1 (the aforementioned exemplified compound (2)). [Synthesis Example 2] (Synthesis of Monomer-2) 13.3 parts of 2-aminobenzimidazole was dissolved in 30 parts of pyridine and heated to 45 °C. On the other hand, 17.1 parts of ethyl 2-methylpropenyloxy isocyanate was added dropwise, and the mixture was further stirred under heating at 50 ° C for 5 hours. While stirring the reaction liquid, 200 parts of distilled water was poured, and the obtained precipitate was separated by filtration and washed to obtain 27.3 parts of the monomer 2 (the above-exemplified compound M-4). (Synthesis of Polymer 2) 5.0 parts of the above-mentioned monomers 2, 37.5 parts of polymethyl methacrylate (AA-6: manufactured by Toagosei Co., Ltd.) having methacryl oxime φ at the terminal, and 7.5 parts of methacrylic acid, And 116.7 parts of 1-methoxy-2-propanol, which was introduced into a three-necked flask which was replaced with nitrogen, and stirred with a stirrer (Nippon Science Co., Ltd.: THREE ONE MOTOR) while allowing nitrogen gas to flow into the flask while raising heat. Up to 78 °C. Add 1 part of dimethyl-2,2'-azobis(2-propionic acid methyl ester) ("V-601" made by Wako Pure Chemical Industries Co., Ltd.) at 78 ° (: heating and stirring) 2 hours. After 2 hours, 1 part of V-601 was further added and stirred under heating for 3 hours to obtain a 30% solution of the polymer 2 (the above-exemplified compound (6)). -55-200821362 [Synthesis Example 3 (Synthesis of Polymer 3) 5.0 parts of the above-mentioned monomers 2, 37.5 parts of polymethyl methacrylate (AA-6: manufactured by Toagosei Co., Ltd.) having methacryl oxime group at the terminal, 7.5 parts of methacrylic acid, 0.90 parts of n-dodecyl mercaptan and 116.7 parts of 1-methoxy-2-propanol were introduced into a nitrogen-substituted three-necked flask and stirred using a stirrer (Xindong Science Co., Ltd.) While heating the nitrogen gas into the flask, the temperature was raised to 75 ° C. 0.26 parts of dimethyl-2,2'-azobis(2-propionic acid methyl ester) was added thereto (Wako Pure Chemical Co., Ltd.) -601"), heating and stirring at 75 ° C for 3 hours. After adding 0.26 parts of V-601 and heating and stirring for 3 hours, 0.26 parts of V-601 was again added and stirred under heating for 3 hours to obtain polymer 3 (previously A 30% solution of the compound (17)) is exemplified. [Synthesis Example 4] (Synthesis of Polymer 4) 5.0 parts of the aforementioned monomers 2, 40.0 parts of polystyrene having a methacryl fluorenyl group φ at the terminal (AS- 6: manufactured by Toagosei Co., Ltd., 5. 〇 methacrylic acid, 0. 76 parts of n-dodecyl mercaptan, and 116.7 parts of 1-methoxy-2-propanol, introduced into a three-necked flask substituted with nitrogen Stirring was carried out using a stirrer (New East Science Co., Ltd.: THREE ONE MOTOR) while heating the nitrogen gas into the flask while heating to 75 ° C. Add 22 parts of dimethyl-2,2'-azo Bis(2-propionic acid methyl ester) ("V-601" manufactured by Wako Pure Chemical Industries Co., Ltd.) was heated and stirred at 75 ° C for 3 hours. Further added 〇 2 2 parts V - 6 0 1 and heated and stirred 3 After the hour, 0 2 2 parts of V - 6 0 1 was further added and stirred under heating for 3 hours to obtain a 30% solution of the polymer 4 (exemplified compound (1 8) described in the above -56 - 200821362). (Synthesis of Polymer 5) 4.0 parts of the above-mentioned monomers 2, 38.5 parts of polymethyl methacrylate having a methacryl oxime group at the terminal (ΑΑ-6: manufactured by Toagosei Co., Ltd.), 7.5 parts of methyl group A succinic anhydride adduct of 2-hydroxyethyl enoate (manufactured by Shin-Nakamura Chemical Co., Ltd., NK ESTER SA: the following structure), 0.43 parts of n-dodecyl mercaptan, and 1 16.7 parts of 1-methoxyl -2 -propanol was introduced into a nitrogen-substituted two-necked flask, and stirred with a stirrer (Nippon Science Co., Ltd.: THREE ONE MOTOR), and the temperature was raised to 75 t while flowing nitrogen into the flask. 0.12 parts of dimethyl-2,2'-azobis(2-propionic acid methyl ester) ("V-601" manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto and heated and stirred at 75 ° C for 3 hours. After further adding 0.12 parts of V-601 and heating and stirring for 3 hours, 12 parts of V-601 was further added and stirred under heating for 3 hours to obtain a 30% solution of polymer 5 (exemplified compound (19)).

φ [化學式6] [合成例6] (聚合物6的合成) 將5.0份前述單體2、35.0份在末端具有甲基丙烯醯基 之聚甲基丙烯酸甲酯(AA-6 ··東亞合成公司製)、5.0份丙烯 酸、5.0甲基丙烯酸苄酯、0.98份正十二烷基硫醇、及116.7 -57- 200821362 份1-甲氧基-2-丙醇,導入已氮氣取代之三口燒瓶中,使用 攪拌機(新東科學(股):THREE ONE MOTOR)攪拌,一邊使 氮氣流入燒瓶內一邊加熱升溫至75 °C。對其添加0.28份二 甲基_2,2’ -偶氮雙(2-丙酸甲酯)(和光純藥(股)製 「V401」)’在75t:進行加熱攪拌3小時。更添加〇.28份 V-601並加熱攪拌3小時後,再次添加0.28份V-601並加 熱攪拌3小時,得到聚合物6(前述之例示化合物(20))的30% 溶液。 [合成例7] (單體-3的合成) 將15.0份2-氫硫基苯并咪唑、13.8份碳酸鉀溶解在30 份二甲基亞颯中,並加熱至45 °C。對此,滴加22.9份氯甲 基苯乙烯,在50°C更進行加熱攪拌5小時。一邊攪拌該反 應液一邊注入200份蒸餾水中,過濾分開所得到的析出物 並洗淨,得到25.6份單體3(前述之例示化合物M-10)。 •(聚合物7的合成) 將5.0份前述單體3、37.5份在末端具有甲基丙烯醯基 之聚甲基丙烯酸甲酯(AA_6:東亞合成公司製)、7.5份甲基 丙烯酸、及116.7份1-甲氧基-2-丙醇’導入已氮氣取代之 三口燒瓶中,使用攪拌機(新東科學(股):THREE ONE MOTOR)攪拌,一邊使氮氣流入燒瓶內一邊加熱升溫至78 。(:。對其添加0.1份二甲基-2,2’ -偶氮雙(2-丙酸甲酯)(和 光純藥(股)製「V - 6 0 1」),在7 8 °C進行加熱攪拌2小時。2 -58- 200821362 小時後,更添加0.1份V-601並加熱攪拌3小時,得到聚 合物7(前述之例示化合物(14))的30%溶液。 [合成例8] (聚合物8的合成) 將7.5份前述單體3、37·5份在末端具有甲基丙烯醯基 之聚甲基丙烯酸甲酯(ΑΑ-6:東亞合成公司製)、5.0份丙烯 酸、0.84份正十二烷基硫醇、及116.7份甲氧基-2-丙醇, 0 導入已氮氣取代之三口燒瓶中,使用攪拌機(新東科學 (股):THREE ONE MOTOR)攪拌,一邊使氮氣流入燒瓶內一 邊加熱升溫至75 °C。對其添加0.24份二甲基-2,2’ ·偶氮雙 (2-丙酸甲酯)(和光純藥(股)製「V-601」),在75。(:進行加 熱攪拌3小時。更添加〇·24份V-601並加熱攪拌3小時後, 再次添加0.24份V-601並加熱攪拌3小時,得到聚合物8(前 述之例示化合物(21))的30%溶液。 [合成例9] _ (單體_4的合成) 將1 6 · 7份2 -氫硫基苯并噻哩、1 3 · 8份碳酸鉀溶解在3 0 份二甲基亞颯中,並加熱至45它。對此,滴加22.9份氯甲 基苯乙烯,在50°C更進行加熱攪拌5小時。一邊攪拌該反 應液一邊注入200份蒸餾水中,過濾分開所得到的析出物 並洗淨,得到26.9份單體4(前述之例示化合物Μ-ll)。 (聚合物9的合成) 將7.5份前述單體4、37.5份在末端具有甲基丙烯醯基 -59- ,200821362 之聚甲基丙烯酸甲酯(AA_6 :東亞合成公司製)、5.0份甲基 丙烯酸、0.74份正十二烷基硫醇、及116.7份1-甲氧基- 2-丙醇,導入已氮氣取代之三口燒瓶中,使用攪拌機(新東科 學(股)·· THREE ONE MOTOR)攪拌,一邊使氮氣流入燒瓶內 一邊加熱升溫至75°C。對其添加0.21份二甲基-2,2’ -偶氮 雙(2-丙酸甲酯)(和光純藥(股)製「V-601」),在75°C進行 加熱攪拌3小時。更添加0.21份V-601並加熱攪拌3小時 ^ 後,再次添加0.21份V-601並加熱攪拌3小時,得到聚合 物9(前述之例示化合物(22))的30%溶液。 [合成例10] (聚合物1 0的合成) 將7.5份前述單體4、37.5份在末端具有甲基丙烯醯基 之聚甲基丙烯酸甲酯(AA-6 :東亞合成公司製)、5.0份甲基 丙烯酸苄酯、〇· 50份正十二烷基硫醇、及116.7份1-甲氧 基-2-丙醇,導入已氮氣取代之三口燒瓶中,使用攪拌機(新 % 東科學(股):THREE ONE MOTOR)攪拌,一邊使氮氣流入燒 瓶內一邊加熱升溫至75 °C。對其添加0.14份二甲基-2,2’ - 偶氮雙(2-丙酸甲酯)(和光純藥(股)製「V-601」),在Ί5Χ: 進行加熱攪拌3小時。更添加0.14份V-601並加熱攪拌3 小時後,再次添加0.14份V-601並加熱攪拌3小時,得到 聚合物10(前述之例示化合物(23))的30%溶液。 [實施例1 ] &lt;顏料分散組成物(R1)的調製&gt; -60- 200821362 混合下述組成(1)之成分,使用均化器以旋轉數 3,0 00r.p.m.攪拌混合3小時,來調製含有顏料之混合溶液。 [組成(1)] • C · I ·顏料紅 2 5 4 · · · 9 0 份 • C.I.顏料紅 177 · · · 10 份 •聚合物1的3 0 %溶液(特定顏料分散劑)· · · 1 5 0份 •2 -乙醯氧基-1-甲氧基丙院 · · ·750份 接著,將由上述所得到的混合溶液,進而藉由使用0.3 ® 毫米Φ氧化鉻珠粒之珠粒分散機DISPERMAT(GETZMANN 公司製)進行分散處理6小時,隨後更瘦用附帶減壓機構之 高壓分散機NANO-3 000-1 0(日本BEE(股)製),在2000公斤 /平方公分的壓力下以流量5 0 0公克/分鐘的方式進行分散 處理。重複該分散處理1 0次,來得到紅色的顏料分散組成 、物(R1)。 &lt;顏料分散組成物的評價&gt; ^ 對所得到的顏料分散組成物(R1)進行以下的評價。 (1) 黏度的測定、評價 對所得到的顏料分散組成物(R 1)使用E型黏度計測定 剛分散後之顏料分散組成物(R1)的黏度W 1及分散後(在室 溫)經過一星期後之顏料分散組成物的黏度〇 2,來評價增 黏的程度。評價結果如下述表1所示。在此,黏度低係能 夠抑制起因於分散劑之黏度上升,表示顏料的分散性及分 散安定性良好。 (2) 對比的測定、評價 -61- 200821362 將所得到的顏料分散組成物(R1)塗布在玻璃基板上,以 乾燥後的塗布膜厚度爲1微米的方式製造試樣。將該試樣 放置在2片偏光板之間,測定偏光軸係平行時及垂直時的 透射光量,將其比作爲對比(該評價法係參考「1 990年第7 回色彩光學硏討會,5 12色顯示10.4”尺寸TFT-LCD用彩 色濾光片,植木、小關、福永、山中」)。測定評價結果係 如下述表1所示。在此,因爲所謂對比高係指顏料爲被高 度微細化狀態且均勻地分散,表示透射率亦即著色力高。 [實施例2〜10] 除了將實施例1之特定顏料分散劑(聚合物1)分別取代 爲在前述合成例2〜1 0各自所得到的特定顏料分散劑之聚 合物2〜聚合物1 〇以外,與實施例丨同樣地進行,來調製紅 色的顏料分散組成物(R2)〜(R 10),並進行與實施例1同樣的 評價。結果如下述表1所示。 [實施例1 1 ] • 除了將實施例1之紅色的顏料分散組成物取代爲使用 含有下述組成(2)的綠色顏料之混合溶液所得到的顏料分 散組成物以外,與實施例1同樣地進行,來調製綠色的顏 料分散組成物(G1),並進行與實施例1同樣的評價。結果 如下述表2所示。 [組成(2)] • C · I ·顏料綠3 6 · · · 6 0份 • C · I ·顏料黃 1 5 0 · · · 4 0 份 -62- 200821362 • 1 5 0 份 • 75 0 份 •聚合物1的3 0 %溶液(特定顏料分散劑) • 2-乙醯氧基-1-甲氧基丙烷 [實施例12〜20] 除了將貫施例1 1中所用之特定顏料分散劑(聚合物i) 取代爲前述聚合物2〜聚合物1()(特定顏料分散劑)以外,與 貫施例1 1同樣地進行,來調製綠色的顏料分散組成物 (G2)〜(G10) ’並進行與實施例U同樣的評價。結果如下述 表2所示。 [實施例21] 除了將貫施例1之紅色的顏料分散組成物取代爲使用 含有下述組成(3)的藍色顏料之混合溶液所得到的藍色顏 料分散組成物以外,與實施例1同樣地進行,來調製藍色 的顏料分散組成物(B1),並進行與實施例丨同樣的評價。 結果如下述表3所示。 [組成(3 )] • · · 85 份 • · · 15 份 • · · 1 5 0 份 • · · 750 份 • C.I.顏料藍15 : 6 • C · I.顏料紫2 3 •聚合物1的3 0 %溶液(特定顏料分散劑) • 2-乙醯氧基-^甲氧基丙烷 [實施例2 2〜3 0 ] 除了將實施例2丨之聚合物丨(特定顏料分散劑)各自取 代爲聚合物2〜聚合物1()(特定顏料分散劑)以外,與實施例 21同樣地進行,來調製藍色的顏料分散組成物 -63- 200821362 (B1)〜(BIO),並進行與實施例21同樣的評價。結果如下述 表3所示。 [比較例1] 除了將實施例1之聚合物1 (特定顏料分散劑)取代爲 EFKA4047(EFKA公司製)(以下稱爲D·1)以外,與實施例i 同樣地進行,來調製紅色的顏料分散組成物(R 1 1 ),並進@ 與實施例1同樣的評價。結果如下述表1所示。 [比較例2] 除了將實施例1之聚合物1(特定顏料分散劑)取代爲 乙烯基咪唑與末端甲基丙烯醯化聚甲基丙烯酸甲酯共聚物 D-2(==15/85[質重比]、重量平均分子重· 30000)以外,跑實 施例1同樣地進行,來調製紅色的顏料分散組成物(R12), 並進行與實施例1同樣的評價。結果如下述表1所示。 [比較例3] 除了將實施例1之聚合物1 (特定顏料分散劑)取代爲甲 • 基丙烯酸與末端甲基丙烯醯化聚甲基丙烯酸甲酯共聚物 D-3(=15/85[質量比]、重量平均分子量:30000)以外,與實 施例1同樣地進行,來調製紅色的顏料分散組成物(R丨3), 並進行與實施例1同樣的評價。結果如下述表1所示。 [比較例4] 除了將實施例1之聚合物1(特定顏料分散劑)取代爲甲 基丙烯酸2-二甲胺基乙酯與末端甲基丙烯醯化聚甲基丙儲 酸甲酯共聚物D-4 (=15/85 [質量比]、重量平均分子量: 20000) -64- 200821362 以外,與實施例1同樣地進行,來調製紅色的顏料分散組 成物(R 1 4),並進行與實施例1同樣的評價。結果如下述表 1所示。 [比較例5 ] 除了將實施例1之聚合物1 (特定顏料分散劑)取代爲下 述結構的單體與末端甲基丙烯醯化聚甲基丙烯酸甲酯共聚 物D-5(=18/82[質量比]、重量平均分子量:20000)以外,與 實施例1同樣地進行,來調製紅色的顏料分散組成物 ^ (R 1 5),並進行與實施例1同樣的評價。結果如下述表1所 示。 [化學式7]φ [Chemical Formula 6] [Synthesis Example 6] (Synthesis of Polymer 6) 5.0 parts of the aforementioned monomers 2, 35.0 parts of polymethyl methacrylate having a methacryl fluorenyl group at the terminal (AA-6 ·· East Asia Synthesis) Company made), 5.0 parts of acrylic acid, 5.0 benzyl methacrylate, 0.98 parts of n-dodecyl mercaptan, and 116.7 -57-200821362 parts of 1-methoxy-2-propanol, introduced into a nitrogen-substituted three-necked flask In the middle, the mixture was stirred with a stirrer (New Zealand Science Co., Ltd.: THREE ONE MOTOR), and the temperature was raised to 75 ° C while flowing nitrogen into the flask. 0.28 parts of dimethyl-2,2'-azobis(2-propionic acid methyl ester) ("V401" manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto at 75 t: heating and stirring for 3 hours. Further, after adding 28 parts of V-601 and heating and stirring for 3 hours, 0.28 parts of V-601 was again added and stirred under heating for 3 hours to obtain a 30% solution of polymer 6 (exemplified compound (20) described above). [Synthesis Example 7] (Synthesis of Monomer-3) 15.0 parts of 2-hydrothiobenzimidazole and 13.8 parts of potassium carbonate were dissolved in 30 parts of dimethylammonium and heated to 45 °C. On the other hand, 22.9 parts of chloromethylstyrene was added dropwise, and the mixture was further heated and stirred at 50 ° C for 5 hours. While stirring the reaction liquid, 200 parts of distilled water was poured, and the obtained precipitate was separated by filtration and washed to obtain 25.6 parts of monomer 3 (exemplified compound M-10 described above). • (Synthesis of Polymer 7) 5.0 parts of the above-mentioned monomers 3, 37.5 parts of polymethyl methacrylate (AA_6: manufactured by Toagosei Co., Ltd.) having a methacryl oxime group at the terminal, 7.5 parts of methacrylic acid, and 116.7 The 1-methoxy-2-propanol was introduced into a nitrogen-substituted three-necked flask, and stirred with a stirrer (New Zealand Science Co., Ltd.: THREE ONE MOTOR), and heated to a temperature of 78 while flowing nitrogen into the flask. (: Add 0.1 part of dimethyl-2,2'-azobis(2-propionic acid methyl ester) ("V-60-1" made by Wako Pure Chemical Industries Co., Ltd.) at 7 8 °C Heating and stirring were carried out for 2 hours. After 2 -58 - 200821362 hours, 0.1 part of V-601 was further added and stirred under heating for 3 hours to obtain a 30% solution of the polymer 7 (exemplified compound (14)). [Synthesis Example 8] (Synthesis of Polymer 8) 7.5 parts of the above-mentioned monomer 3, 37·5 parts of polymethyl methacrylate having a methacryl fluorenyl group at the end (ΑΑ-6: manufactured by Toagosei Co., Ltd.), 5.0 parts of acrylic acid, 0.84 a portion of n-dodecyl mercaptan and 116.7 parts of methoxy-2-propanol, 0 was introduced into a nitrogen-substituted three-necked flask, and stirred with a stirrer (Newton Science: THREE ONE MOTOR) while nitrogen was applied. The temperature was raised to 75 ° C while flowing into the flask, and 0.24 parts of dimethyl-2,2'-azobis(2-propionate methyl ester) ("V-601" manufactured by Wako Pure Chemical Industries Co., Ltd.) was added thereto. At 75. (: heating and stirring for 3 hours. After adding 24 parts of V-601 and heating and stirring for 3 hours, 0.24 parts of V-601 was added again and heated and stirred for 3 hours to obtain polymer 8 (previously A 30% solution of the compound (21)) is exemplified. [Synthesis Example 9] _ (Synthesis of monomer_4) 1 6 · 7 parts of 2-hydrothiobenzothiazinium, 1 3 · 8 parts of potassium carbonate is dissolved in 30 parts of dimethyl hydrazine and heated to 45. To this, 22.9 parts of chloromethylstyrene was added dropwise, and the mixture was further heated and stirred at 50 ° C for 5 hours, while 200 parts of distilled water was poured while stirring the reaction liquid. The precipitate obtained was separated by filtration and washed to obtain 26.9 parts of the monomer 4 (the above-exemplified compound Μ-ll). (Synthesis of the polymer 9) 7.5 parts of the aforementioned monomers 4, 37.5 parts have a nail at the end. Methyl methacrylate-59-, 200821362 polymethyl methacrylate (AA_6: manufactured by Toagosei Co., Ltd.), 5.0 parts of methacrylic acid, 0.74 parts of n-dodecyl mercaptan, and 116.7 parts of 1-methoxy- 2-propanol was introduced into a three-necked flask which was replaced with nitrogen, and stirred with a stirrer (Nippon Scientific Co., Ltd., THREE ONE MOTOR), and the temperature was raised to 75 ° C while flowing nitrogen gas into the flask. 0.21 part was added thereto. Dimethyl-2,2'-azobis(2-propionic acid methyl ester) ("V-601" manufactured by Wako Pure Chemical Co., Ltd.), heated at 75 ° C After mixing for 3 hours, 0.21 part of V-601 was further added and stirred under heating for 3 hours. Then, 0.21 part of V-601 was again added and stirred under heating for 3 hours to obtain a 30% solution of the polymer 9 (the aforementioned exemplified compound (22)). [Synthesis Example 10] (Synthesis of Polymer 10) 7.5 parts of the above-mentioned monomers 4 and 37.5 parts of polymethyl methacrylate (AA-6: manufactured by Toagosei Co., Ltd.) having a methyl methacrylate group at the terminal, 5.0 Part of benzyl methacrylate, hydrazine · 50 parts of n-dodecyl mercaptan, and 116.7 parts of 1-methoxy-2-propanol, introduced into a nitrogen-substituted three-necked flask, using a blender (New % East Science ( Share): THREE ONE MOTOR) Stir and heat to 75 °C while flowing nitrogen into the flask. 0.14 parts of dimethyl-2,2'-azobis(2-propionic acid methyl ester) ("V-601" manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto, and the mixture was stirred under heating for 3 hours. After further adding 0.14 parts of V-601 and heating and stirring for 3 hours, 0.14 parts of V-601 was again added and stirred under heating for 3 hours to obtain a 30% solution of the polymer 10 (the aforementioned exemplified compound (23)). [Example 1] &lt;Preparation of Pigment Dispersion Composition (R1)&gt; -60-200821362 The components of the following composition (1) were mixed, and stirred and mixed for 3 hours at a number of revolutions of 3,00 rpm using a homogenizer. To prepare a mixed solution containing a pigment. [Composition (1)] • C · I · Pigment Red 2 5 4 · · · 9 0 parts • CI Pigment Red 177 · · · 10 parts • 30% solution of Polymer 1 (Specific Pigment Dispersant) · · · 1 50 parts • 2 -ethoxymethoxy-1-methoxypropane · · · 750 parts Next, the mixed solution obtained above was dispersed by using beads of 0.3 ® mm Φ chrome oxide beads The machine DISPERMAT (manufactured by GETZMANN) was subjected to dispersion treatment for 6 hours, and then it was thinner and used with a high-pressure disperser NANO-3 000-1 0 (manufactured by Japan BEE Co., Ltd.) with a pressure reducing mechanism under a pressure of 2000 kg/cm 2 Dispersion treatment was carried out at a flow rate of 500 g/min. This dispersion treatment was repeated 10 times to obtain a red pigment dispersion composition and a substance (R1). &lt;Evaluation of Pigment Dispersion Composition&gt; ^ The obtained pigment dispersion composition (R1) was subjected to the following evaluation. (1) Measurement and Evaluation of Viscosity The obtained pigment dispersion composition (R 1 ) was measured for the viscosity W 1 of the pigment dispersion composition (R1) immediately after dispersion and the dispersion (at room temperature) by using an E-type viscometer. The viscosity of the pigment dispersion composition after one week was 〇2 to evaluate the degree of adhesion. The evaluation results are shown in Table 1 below. Here, the low viscosity can suppress the increase in the viscosity of the dispersant, indicating that the dispersibility and dispersion stability of the pigment are good. (2) Measurement and evaluation of comparison -61-200821362 The obtained pigment dispersion composition (R1) was applied onto a glass substrate, and a sample was produced so that the thickness of the coating film after drying was 1 μm. The sample was placed between two polarizing plates, and the amount of transmitted light when the polarization axis was parallel and perpendicular was measured, and the ratio was compared (this evaluation method is referred to as "the 7th color optical begging meeting in 990," 5 12-color display color filter for 10.4" size TFT-LCD, Ueki, Xiaoguan, Fuyong, Shanzhong"). The measurement evaluation results are shown in Table 1 below. Here, the term "high contrast" means that the pigment is highly refined and uniformly dispersed, indicating that the transmittance, that is, the coloring power is high. [Examples 2 to 10] In addition, the specific pigment dispersant (polymer 1) of Example 1 was replaced with the polymer 2 to polymer 1 of the specific pigment dispersant obtained in each of the above Synthesis Examples 2 to 10, respectively. The red pigment dispersion compositions (R2) to (R10) were prepared in the same manner as in Example ,, and the same evaluation as in Example 1 was carried out. The results are shown in Table 1 below. [Example 1 1] The same procedure as in Example 1 was carried out except that the pigment dispersion composition of the red pigment of Example 1 was replaced with the pigment dispersion composition obtained by using the mixed solution of the green pigment of the following composition (2). The green pigment dispersion composition (G1) was prepared and evaluated in the same manner as in Example 1. The results are shown in Table 2 below. [Composition (2)] • C · I · Pigment Green 3 6 · · · 60 parts • C · I · Pigment Yellow 1 5 0 · · · 4 0 parts -62- 200821362 • 1 5 0 parts • 75 0 parts • 30% solution of polymer 1 (specific pigment dispersant) • 2-Ethyloxy-1-methoxypropane [Examples 12 to 20] In addition to the specific pigment dispersant used in Example 11 (Polymer i) The green pigment dispersion composition (G2) to (G10) was prepared in the same manner as in Example 1 except that the polymer 2 to the polymer 1 (polymer (specific pigment dispersant) were used instead. 'The same evaluation as in Example U was carried out. The results are shown in Table 2 below. [Example 21] Example 1 was prepared except that the red pigment dispersion composition of Example 1 was replaced with a blue pigment dispersion composition obtained by using a mixed solution containing the blue pigment of the following composition (3). In the same manner, the blue pigment dispersion composition (B1) was prepared, and the same evaluation as in Example 。 was carried out. The results are shown in Table 3 below. [Composition (3)] • · · 85 parts • · · 15 parts • · · 1 50 parts • · · 750 parts • CI Pigment Blue 15 : 6 • C · I. Pigment Violet 2 3 • Polymer 1 of 3 0% solution (specific pigment dispersant) • 2-Ethyloxy-methoxypropane [Example 2 2 to 3 0 ] except that the polymer oxime (specific pigment dispersant) of Example 2 was each replaced with In the same manner as in Example 21 except that the polymer 2 to the polymer 1 () (specific pigment dispersant) were used, the blue pigment dispersion composition-63-200821362 (B1) to (BIO) was prepared and carried out. Example 21 was evaluated in the same manner. The results are shown in Table 3 below. [Comparative Example 1] A red color was prepared in the same manner as in Example i except that the polymer 1 (specific pigment dispersant) of Example 1 was replaced by EFKA 4047 (manufactured by EFKA Co., Ltd.) (hereinafter referred to as D·1). The pigment dispersion composition (R 1 1 ) was subjected to the same evaluation as in Example 1. The results are shown in Table 1 below. [Comparative Example 2] except that the polymer 1 (specific pigment dispersant) of Example 1 was substituted with vinylimidazole and terminal methacrylic acid polymethyl methacrylate copolymer D-2 (==15/85 [ The red pigment dispersion composition (R12) was prepared in the same manner as in Example 1 except that the mass-to-weight ratio and the weight average molecular weight (30000) were the same as in Example 1. The same evaluation as in Example 1 was carried out. The results are shown in Table 1 below. [Comparative Example 3] In addition to the replacement of the polymer 1 (specific pigment dispersant) of Example 1 with methyl methacrylate and terminal methacrylic acid polymethyl methacrylate copolymer D-3 (= 15/85 [ The red pigment dispersion composition (R丨3) was prepared in the same manner as in Example 1 except that the mass ratio and the weight average molecular weight: 30000), and the same evaluation as in Example 1 was carried out. The results are shown in Table 1 below. [Comparative Example 4] In addition to the replacement of the polymer 1 (specific pigment dispersant) of Example 1 with 2-dimethylaminoethyl methacrylate and a terminal methacrylic acid polymethyl methacrylate copolymer In the same manner as in Example 1, except that D-4 (=15/85 [mass ratio], weight average molecular weight: 20000) -64-200821362, a red pigment dispersion composition (R 1 4) was prepared and subjected to The same evaluation as in Example 1 was carried out. The results are shown in Table 1 below. [Comparative Example 5] Except that the polymer 1 (specific pigment dispersant) of Example 1 was substituted with a monomer having the following structure and a terminal methacrylic acid polymethyl methacrylate copolymer D-5 (=18/ In the same manner as in Example 1, except that 82 [mass ratio] and weight average molecular weight: 20000), a red pigment dispersion composition (R 1 5) was prepared, and the same evaluation as in Example 1 was carried out. The results are shown in Table 1 below. [Chemical Formula 7]

[比較例6 ] 除了將實施例1之聚合物1 (特定顏料分散劑)取代爲下 Φ 述結構的單體與末端甲基丙烯醯化聚甲基丙嫌酸甲酯共聚 物D-6(=18/82[質量比]、重量平均分子量:2000〇)以外,與 實施例1同樣地進行’來調製紅色的顏料分散組成物 (R1 6),並進行與實施例1同樣的評價。結果如下述表i所 -65- 200821362 [化學式8][Comparative Example 6] except that the polymer 1 (specific pigment dispersant) of Example 1 was substituted with the monomer of the structure of the lower Φ and the terminal methacrylic acid polymethyl methacrylate copolymer D-6 ( In the same manner as in Example 1, except that the pigment dispersion composition (R16) of red was prepared, the same evaluation as in Example 1 was carried out in the same manner as in Example 1 except that the ratio was 18/82 [mass ratio]. The results are as shown in the following table -65-200821362 [Chemical Formula 8]

[比較例7〜1 2 ] 除了將實施例11之聚合物1(特定顏料分散劑)各自變 更爲目U述共聚物D -1〜D 6中任一者以外,與實施例1 1同樣 地進行,來調製綠色的顏料分散組成物(G11)〜(G16),並進 行與實施例1 1同樣的評價。結果如下述表2所示。 [比較例1 3〜1 8 ] 除了將實施例2 1之前述聚合物1 (特定顏料分散劑)各 自取代爲前述共聚物D-1〜D6中任一者以外’與實施例21 同樣地進行,來調製藍色的顏料分散組成物(B 1 1)〜(B 1 6) ’ 並進行與實施例2 1同樣的評價。結果如下述表3所不。 -66- 200821362 [表1] 紅色顏料 分散組成物 顏料分散劑 剛分散後的 黏度(mPa · s) 1星期後的 黏度(mPa · s) 對比 實施例1 R1 聚合物1 12 13 1250 實施例2 R2 聚合物2 8 9 1350 實施例3 R3 聚合物3 7 8 1350 實施例4 R4 聚合物4 8 9 1350 實施例5 R5 聚合物5 9 10 1350 實施例6 R6 聚合物6 8 9 1350 實施例7 R7 聚合物7 10 10 1300 實施例8 R8 聚合物8 9 10 1350 實施例9 R9 聚合物9 8 9 1350 實施例10 R10 聚合物10 8 8 1350 比較例1 R11 D-1 25 250 1100 比較例2 R12 D-2 20 400 950 比較例3 R13 D-3 1200以上 凝膠化 900 比較例4 R14 D-4 15 75 1150 比較例5 R15 D-5 20 80 1150 比較例6 R16 D-6 15 70 1150 -67- 200821362[Comparative Example 7 to 1 2] The same procedure as in Example 1 1 except that the polymer 1 (specific pigment dispersant) of Example 11 was changed to any of the copolymers D-1 to D6. The green pigment dispersion compositions (G11) to (G16) were prepared, and the same evaluation as in Example 1 was carried out. The results are shown in Table 2 below. [Comparative Example 1 3 to 1 8] The same procedure as in Example 21 was carried out except that each of the polymer 1 (specific pigment dispersant) of Example 21 was replaced with any of the above copolymers D-1 to D6. The blue pigment dispersion composition (B 1 1) to (B 1 6) ' was prepared and evaluated in the same manner as in Example 21. The results are as shown in Table 3 below. -66- 200821362 [Table 1] Viscosity of red pigment dispersion composition pigment dispersant immediately after dispersion (mPa · s) Viscosity after 1 week (mPa · s) Comparative Example 1 R1 Polymer 1 12 13 1250 Example 2 R2 Polymer 2 8 9 1350 Example 3 R3 Polymer 3 7 8 1350 Example 4 R4 Polymer 4 8 9 1350 Example 5 R5 Polymer 5 9 10 1350 Example 6 R6 Polymer 6 8 9 1350 Example 7 R7 Polymer 7 10 10 1300 Example 8 R8 Polymer 8 9 10 1350 Example 9 R9 Polymer 9 8 9 1350 Example 10 R10 Polymer 10 8 8 1350 Comparative Example 1 R11 D-1 25 250 1100 Comparative Example 2 R12 D-2 20 400 950 Comparative Example 3 R13 D-3 1200 or more gelation 900 Comparative Example 4 R14 D-4 15 75 1150 Comparative Example 5 R15 D-5 20 80 1150 Comparative Example 6 R16 D-6 15 70 1150 -67- 200821362

[表2] 綠色顏料 分散組成物 顏料分散劑 岡!J分散後的 黏度(mPa · s) 1星期後的 黏度(mPa · s) 對比 實施例11 G1 聚合物1 14 14 1450 實施例12 G2 聚合物2 10 11 1500 實施例13 G3 聚合物3 9 9 1550 實施例14 G4 聚合物4 10 10 1550 實施例15 G5 聚合物5 11 11 1500 實施例16 G6 聚合物6 10 11 1500 實施例17 G7 聚合物7 15 16 1500 實施例18 G8 聚合物8 12 13 1500 實施例19 G9 聚合物9 13 14 1500 實施例20 G10 聚合物10 13 13 1550 比較例7 G11 D4 20 85 1250 比較例8 G12 D-2 18 150 1150 比較例9 G13 D-3 1200以上 凝膠化 1000 比較例10 G14 D-4 15 70 1250 比較例11 G15 D-5 15 75 1250 比較例12 G16 D-6 • 15 65 1250 -68- 200821362 [表3] 藍色顏料 分散組成物 顏料分散劑 剛分散後的 黏度(mPa · s) 1星期後的 黏度(mPa · s) 對比 實施例21 B1 聚合物1 16 16 1 1100 實施例22 B2 聚合物2 12 13 1150 實施例23 B3 聚合物3 11 11 1200 實施例24 B4 聚合物4 12 12 1200 實施例25 B5 聚合物5 12 13 1200 實施例26 B6 聚合物6 12 13 1200 實施例27 B7 聚合物7 12 14 1100 實施例28 B8 聚合物8 12 13 1150 實施例29 B9 聚合物9 13 14 . 1150 實施例30 B10 聚合物10 13 13 1150 比較例13 B11 D-1 125 360 950 比較例14 B12 D-2 225 490 900 比較例15 B13 D-3 900 凝膠化 700 比較例16 B14 D-4 250 500 850 比較例17 B15 D-5 300 720 800 比較例18 B16 D-6 270 900 850 如表1〜表3所示,得知使用本發明之聚合物1〜10(特定 顏料分散劑)之實施例的顏料分散組成物,任一者之組成物 的黏度低,顏料分散性、分散安定性優良,使用該顏料分 散組成物所得到的被膜能夠得到高對比。使用本發明的顏 料分散組成物所得到的被膜能達成高對比,推測係顏料粒 -69- 200821362 子以被微細化狀態均勻地分散之緣故。 另一方面,得知使用本發明之範圍外之眾所周知的顏料 分散劑之比較例的顏料分散組成物,其黏度較高,顏料的 分散性與本發明之物比較時較低,分散安定性亦較差,使 用該顏料分散組成物所得到的被膜無法得到充分的對比。 [實施例31] &lt;光硬化性組成物之調製&gt; 在實施例1所得到之含有紅色顏料之顏料分散組成物 (R 1 ),更添力D下述組成(4)所記載之各成分並攪拌混合,來 調製含有紅色顏料之本發明的光硬化性組成物(彩色光阻 液)。 [組成(4)] •二新戊四醇六丙烯酸酯 · · · 80份 (光聚合性化合物) • 4-[鄰溴-對Ν,Ν·二(乙氧基羰基)胺基苯基]-2,6-二(三氯甲 φ 基)-S-三阱 · · · 30份 (光聚合引發劑) •甲基丙烯酸苄酯/甲基丙烯酸( = 70/30[質量比])共聚物 (重量平均分子量:10,000)之 2-乙醯氧基-1-甲氧基丙烷溶液(固體成分30%) · · 300份 (鹼可溶性樹脂) • 2-乙醯氧基-1-甲氧基丙烷(溶劑) · · · 390份 &lt;使用光硬化性組成物之彩色濾光片的製造&gt; -70- 200821362 將所得到的光硬化性組成物(彩色光阻液),以使色濃度 指標之X値成爲0.650的方式塗布在100毫米XI 00毫米的 玻璃基板( 1 7 3 7、CORNING公司製)上,並在90°C的烘箱乾 燥60秒(預烘烤)。隨後,對塗膜的全面,以200m〗/cm2(照 度 20mW/cm2)曝光,使用鹼顯影液 CDK-1 (FUJI FILM ELECTRONICS MATERIALS (股)製)之1 %水溶液覆蓋曝光後 的塗膜,並靜置60秒。靜置後,噴淋狀地噴灑純水來洗掉 顯影液。然後,將如上述施行過曝光及顯影之塗膜,以220 ® t的烘箱加熱處理(後烘烤)1小時,並在玻璃基板上形成彩 色濾光片用著色圖案(著色樹脂被膜),來製造著色濾光基 板(彩色濾光片)。 &lt;彩色濾光片的評價&gt; 對所製造的著色濾光基板(彩色濾光片)進行如下的評 價。結果如下述表4所示。 (3) 對比 在附有著色樹脂被膜之著色濾光基板的上下方各自放 置1片偏光板而將著色樹脂被膜夾住,使用TOPCON公司 製的BM-5測定偏光板平行時的亮度及垂直時的亮度,將平 行時的亮度除以垂直時的亮度所得到的値(=平行時的亮度 /垂直時的亮度),作爲用以評價對比的指標。値越大表示 具有高對比。 (4) 顯影性 使用光學顯微鏡觀察在曝光步驟中光未照射的區域(未 曝光部)是否有殘渣,來評價顯影性。 -71- 200821362 〇:在未曝光部完全未發現殘渣。 △:雖然在未曝光部發現些微的殘渣,但是係實# ± m w 問題的程度。 X :在未曝光部發現顯著的殘渣。 [實施例32〜40] 除了將實施例31之顏料分散組成物(R1)取代爲實施例 2〜1 0所得到的顏料分散組成物(R 2)〜(R 1 〇)以外,與實j拒例 3 1同樣地進行來調製光硬化性組成物(彩色光阻液)。使用 該彩色光阻液來製造著色濾光基板(彩色濾光片),進行與 實施例3 1同樣的評價。結果如下述表4所示。 [實施例41] 在實施例1 1所得到之顏料分散組成物(G 1 ),更添加下 述組成(5)所記載之各成分並攪拌混合,來調製含有綠色顏 料之本發明的光硬化性組成物(彩色光阻液)。 [組成(5)] φ •二新戊四醇六丙烯酸酯 · · · 50份 (光聚合性化合物) ’ • 4-[鄰溴-對N,N-二(乙氧基羰基)胺基苯基]-2,6-二(三氯甲 基)-S-三畊 · · · 20份 (光聚合引發劑) •甲基丙烯酸苄酯/甲基丙烯酸( = 70/30[質量比])共聚物 (重量平均分子量:10,000)之 2-乙醯氧基-1-甲氧基丙烷溶液(固體成分30%) · · · 70 -72- 200821362 份 (鹼可溶性樹脂) • 2-乙醯氧基-1-甲氧基丙烷(溶劑) · · · 160份 &lt;使用光硬化性組成物之彩色濾光片的製造及評價&gt; 將所得到的光硬化性組成物(彩色光阻液),以使色濃度 指標之y値成爲0.600的方式塗布在100毫米xlOO毫米的 玻璃基板( 1 7 37、CORNING公司製)上,並在90 °C的烘箱乾 燥60秒(預烘烤)。隨後,對塗膜的全面,以200mJ/cm2(照 度 20mW/cm2)曝光,使用鹼顯影液 CDK-1 (FUJI FILM ELECTRONICS M A TE RIA L S (股)製)之1 %水溶液覆蓋曝光後 的塗膜,並靜置60秒。靜置後,噴淋狀地噴灑純水來洗掉 顯影液。然後,將如上述施行過曝光及顯影之塗膜,以220 °C的烘箱加熱處理(後烘烤)1小時,並在玻璃基板上形成彩 色濾光片用著色圖案(著色樹脂被膜),來製造著色濾光基 板(彩色濾光片)。 與實施例31的評價同樣地進行所製得之著色濾光基板 的對比測定及顯影性評價。結果如下述表5所示。 [實施例4 2 - 5 0 ] 除了將實施例4 1之顏料分散組成物(G 1)取代爲實施例 12〜20所得到的顏料分散組成物(G2)〜(G1〇)以外,與實施例 4 1同樣地進行來調製光硬化性組成物(彩色光阻液)。使用 該彩色光阻液來製造著色濾光基板(彩色濾光片),進行與 實施例3 1同樣的評價。結果如下述表5所示。 -73- 200821362 [實施例5 1 ] 在貫施例2 1所得到之顏料分散組成物(b 1 ),更添加下 述組成(6)所記載之各成分並攪拌混合,來調製含有藍色顏 料之本發明的光硬化性組成物(彩色光阻液)。 [組成(6)] •二新戊四醇六丙烯酸酯 · · · 1 5 0份 (光聚合性化合物) ^ · 4-[鄰溴-對N,N-二(乙氧基羰基)胺基苯基]-2,6-二(三氯甲 基)-S -二哄 ...60 份 (光聚合引發劑) •甲基丙烯酸苄酯/甲基丙烯酸( = 70/30 [質量比])共聚物 (重量平均分子量:1 0,000)之 2-乙醯氧基-卜甲氧基丙烷溶液(固體成分30%) ·· 600份 (鹼可溶性樹脂) •2·乙醯氧基-1-甲氧基丙烷(溶劑) · · · 1240份 Φ &lt;使用光硬化性組成物之彩色濾光片的製造及評價&gt; 將已調製的光硬化性組成物(彩色光阻液),以使色濃度 指標之y値爲0.090的方式塗布在100毫米xl 00毫米的玻 璃基板( 1 7 37、CORNING公司製)上,並在90°C的烘箱乾燥 60秒(預烘烤)。隨後,對塗膜的全面,以200m〗/cm2(照度 20mW/cm2)曝光,使用鹼顯影液 CDK-1(FUJI FILM ELECTRONICS M A TE RIA L S (股)製)之l%7jc溶液覆蓋曝光後 的塗膜,並靜置60秒。靜置後,噴淋狀地噴灑純水來洗掉 -74- 200821362 顯影液。然後’將如上述施行過曝光及顯影之塗膜’以220 °C的烘箱加熱處理(後烘烤)1小時,並在玻璃基板上形成彩 色濾光片用著色圖案(著色樹脂被膜)’來製造者色濾光基 板(彩色濾光片)。 與實施例31同樣地進行所製造之著色濾光基板的對比 測定及顯影性評價。結果如下述表6所示。 [實施例52〜60] φ 除了將實施例5 1之顏料分散組成物(B 1)取代爲實施例 22〜30所得到的顏料分散組成物(B 2)〜(B 10)以外,與實施例 5 1同樣地進行來調製光硬化性組成物(彩色光阻液)。使用 該彩色光阻液來製造著色濾光基板(彩色濾光片),進行與 實施例3 1同樣的評價。結果如下述表6所示。 [比較例1 9〜2 4 ] 除了將實施例3 1之實施例1所得到的顏料分散組成物 鲁 (R1)取代爲比較例 1〜6所得到的顏料分散組成物 (Rl 1)〜(R 16)以外,與實施例31同樣地進行來調製光硬化性 組成物(彩色光阻液)。使用該彩色光阻液來製造著色濾光 基板(彩色濾光片),進行與實施例3 1同樣的評價。結果如 下述表4所示。 [比較例25〜30] 除了將實施例41之實施例11所得到的顏料分散組成物 (G 1)取代爲比較例7〜1 2所得到的顏料分散組成物(〇 η )〜(〇 1 6) -75 - 200821362 以外,與實施例4 1同樣地進行來調製光硬化性組成物(彩 色光阻液)。使用該彩色光阻液來製造著色濾光基板(彩色 濾光片)’進行與實施例41同樣的評價。結果如下述表5 所示。 [比較例31〜36] 除了將實施例5 1之實施例2 1所得到的顏料分散組成物 (B 1)取代爲比較例 1 3〜1 8所得到的顏料分散組成物 φ (B 11)〜(B 16)以外,與實施例51同樣地進行來調製光硬化性 組成物(彩色光阻液)。使用該彩色光阻液來製造著色濾光 基板(彩色濾光片),進行與實施例5 1同樣的評價。結果如 下述表6所示。 、 -76- 200821362[Table 2] Green pigment dispersion composition Pigment dispersant ! J viscosity after dispersion (mPa · s) Viscosity after 1 week (mPa · s) Comparative Example 11 G1 Polymer 1 14 14 1450 Example 12 G2 Polymerization 2 10 11 1500 Example 13 G3 Polymer 3 9 9 1550 Example 14 G4 Polymer 4 10 10 1550 Example 15 G5 Polymer 5 11 11 1500 Example 16 G6 Polymer 6 10 11 1500 Example 17 G7 Polymerization 7 15 16 1500 Example 18 G8 Polymer 8 12 13 1500 Example 19 G9 Polymer 9 13 14 1500 Example 20 G10 Polymer 10 13 13 1550 Comparative Example 7 G11 D4 20 85 1250 Comparative Example 8 G12 D-2 18 150 1150 Comparative Example 9 G13 D-3 1200 or more gelation 1000 Comparative Example 10 G14 D-4 15 70 1250 Comparative Example 11 G15 D-5 15 75 1250 Comparative Example 12 G16 D-6 • 15 65 1250 -68- 200821362 [Table 3] Blue pigment dispersion composition Pigment dispersant viscosity just after dispersion (mPa · s) Viscosity after 1 week (mPa · s) Comparative Example 21 B1 Polymer 1 16 16 1 1100 Example 22 B2 Polymer 2 12 13 1150 Example 23 B3 Polymer 3 11 11 1200 Example 24 B4 Polymer 4 12 12 1200 Example 25 B5 Polymer 5 12 13 1200 Example 26 B6 Polymer 6 12 13 1200 Example 27 B7 Polymer 7 12 14 1100 Example 28 B8 Polymer 8 12 13 1150 Example 29 B9 Polymer 9 13 14 . 1150 Example 30 B10 Polymer 10 13 13 1150 Comparative Example 13 B11 D-1 125 360 950 Comparative Example 14 B12 D-2 225 490 900 Comparative Example 15 B13 D-3 900 Gelation 700 Comparative Example 16 B14 D -4 250 500 850 Comparative Example 17 B15 D-5 300 720 800 Comparative Example 18 B16 D-6 270 900 850 As shown in Tables 1 to 3, it was found that the polymers 1 to 10 (specific pigment dispersants) of the present invention were used. In the pigment dispersion composition of the example, the composition of any of the pigments has a low viscosity, and is excellent in pigment dispersibility and dispersion stability, and a film obtained by using the pigment dispersion composition can be highly contrasted. The film obtained by using the pigment dispersion composition of the present invention can achieve high contrast, and it is estimated that the pigment particles -69 - 200821362 are uniformly dispersed in a finely divided state. On the other hand, it is known that the pigment dispersion composition of the comparative example using the well-known pigment dispersant outside the scope of the present invention has a high viscosity, and the dispersibility of the pigment is lower than that of the present invention, and the dispersion stability is also Poorly, the film obtained by dispersing the composition using the pigment could not be sufficiently contrasted. [Example 31] &lt;Preparation of photocurable composition&gt; The pigment dispersion composition (R 1 ) containing the red pigment obtained in Example 1 was further added to each of the following compositions (4). The components were stirred and mixed to prepare a photocurable composition (color resist liquid) of the present invention containing a red pigment. [Composition (4)] • Dipentaerythritol hexaacrylate · · · 80 parts (photopolymerizable compound) • 4-[o-bromo-p-oxime, Ν·bis(ethoxycarbonyl)aminophenyl] -2,6-bis(trichloromethane)-S-tripper · · · 30 parts (photopolymerization initiator) • benzyl methacrylate/methacrylic acid (= 70/30 [mass ratio]) copolymerization (weight average molecular weight: 10,000) 2-ethoxycarbonyl-1-methoxypropane solution (solid content 30%) · · 300 parts (alkali soluble resin) • 2-Ethyloxy-1-methoxy Propane (solvent) · · · 390 parts &lt;Production of color filter using photocurable composition&gt; -70-200821362 The obtained photocurable composition (color resist liquid) is used to make color The X値 of the concentration index was applied to a glass substrate of 100 mm XI 00 mm (manufactured by CORNING Co., Ltd.) in a manner of 0.650, and dried in an oven at 90 ° C for 60 seconds (prebaking). Subsequently, the entire coating film was exposed to 200 m/cm 2 (illuminance: 20 mW/cm 2 ), and the exposed coating film was covered with a 1% aqueous solution of an alkali developer CDK-1 (manufactured by FUJI FILM ELECTRONICS MATERIALS). Allow to stand for 60 seconds. After standing, spray pure water spray to wash off the developer. Then, the coating film subjected to the exposure and development as described above is heat-treated (post-baked) in an oven of 220 ® t for 1 hour, and a coloring pattern (colored resin film) for color filters is formed on the glass substrate. A colored filter substrate (color filter) is produced. &lt;Evaluation of color filter&gt; The following colored filter substrate (color filter) was evaluated as follows. The results are shown in Table 4 below. (3) In contrast, one polarizing plate was placed on the upper and lower sides of the colored filter substrate with the colored resin film to sandwich the colored resin film, and the brightness and vertical direction when the polarizing plates were parallel were measured using BM-5 manufactured by TOPCON Co., Ltd. The brightness obtained by dividing the brightness in parallel by the brightness in the vertical direction (= brightness in parallel/brightness in vertical) is used as an index for evaluating contrast. A larger 表示 indicates a high contrast. (4) Developability The developability was evaluated by observing whether or not there was a residue in the region (unexposed portion) where the light was not irradiated in the exposure step by an optical microscope. -71- 200821362 〇: No residue was found in the unexposed part. △: Although a slight residue was found in the unexposed portion, the degree of the #±m w problem was obtained. X : Significant residue was found in the unexposed portion. [Examples 32 to 40] Except that the pigment dispersion composition (R1) of Example 31 was replaced with the pigment dispersion composition (R 2) to (R 1 〇) obtained in Examples 2 to 10, Rejection 3 1 was carried out in the same manner to prepare a photocurable composition (color resist liquid). The colored filter substrate (color filter) was produced using the color resist liquid, and the same evaluation as in Example 31 was carried out. The results are shown in Table 4 below. [Example 41] The pigment dispersion composition (G 1 ) obtained in Example 1 was further added with the components described in the following composition (5), and stirred and mixed to prepare a photocuring of the present invention containing a green pigment. Sex composition (color photoresist). [Composition (5)] φ • Dipentaerythritol hexaacrylate · · · 50 parts (photopolymerizable compound) ' • 4-[o-bromo-p-N,N-bis(ethoxycarbonyl)aminobenzene Base]-2,6-bis(trichloromethyl)-S-three tillage · · · 20 parts (photopolymerization initiator) • benzyl methacrylate/methacrylic acid (= 70/30 [mass ratio]) Copolymer (weight average molecular weight: 10,000) 2-Ethyloxy-1-methoxypropane solution (solid content 30%) · · · 70 -72- 200821362 parts (alkali soluble resin) • 2-Ethyloxyl Base-1-methoxypropane (solvent) · · · 160 parts &lt;Manufacturing and evaluation of color filter using photocurable composition&gt; The obtained photocurable composition (color resist liquid) It was applied to a glass substrate (manufactured by CORNING Co., Ltd.) of 100 mm x 100 mm so that the y 色 of the color density index was 0.600, and dried in an oven at 90 ° C for 60 seconds (prebaking). Subsequently, the entire coating film was exposed to 200 mJ/cm 2 (illuminance: 20 mW/cm 2 ), and the exposed coating film was covered with an aqueous solution of an alkali developer CDK-1 (FUJI FILM ELECTRONICS MA TE RIA LS (manufactured by FUJI FILS)). And let stand for 60 seconds. After standing, spray pure water spray to wash off the developer. Then, the coating film subjected to the exposure and development as described above was heat-treated (post-baked) in an oven at 220 ° C for 1 hour, and a coloring pattern (colored resin film) for color filters was formed on the glass substrate. A colored filter substrate (color filter) is produced. Comparative measurement and developability evaluation of the obtained colored filter substrate were carried out in the same manner as in the evaluation of Example 31. The results are shown in Table 5 below. [Example 4 2 - 50] In addition to the pigment dispersion composition (G 1) of Example 41, which was replaced by the pigment dispersion compositions (G2) to (G1〇) obtained in Examples 12 to 20, Example 4 1 The photocurable composition (color resist liquid) was prepared in the same manner. The colored filter substrate (color filter) was produced using the color resist liquid, and the same evaluation as in Example 31 was carried out. The results are shown in Table 5 below. -73-200821362 [Example 5 1] The pigment dispersion composition (b 1 ) obtained in Example 2 1 was further added with the components described in the following composition (6), and stirred and mixed to prepare a blue color. A photocurable composition (color resist liquid) of the present invention. [Composition (6)] • Dipentaerythritol hexaacrylate · · · 150 parts (photopolymerizable compound) ^ · 4-[o-bromo-p-N,N-bis(ethoxycarbonyl)amino group Phenyl]-2,6-bis(trichloromethyl)-S-dioxin...60 parts (photopolymerization initiator) • benzyl methacrylate/methacrylic acid (= 70/30 [mass ratio] Copolymer (weight average molecular weight: 10,000) 2-ethyloxy-p-methoxypropane solution (solid content 30%) ·· 600 parts (alkali-soluble resin) •2·Ethyloxy-1- Methoxypropane (solvent) · · · 1240 parts Φ &lt;Production and evaluation of color filter using photocurable composition&gt; The prepared photocurable composition (color resist liquid) is made so that The color density index was applied to a glass substrate (manufactured by CORNING Co., Ltd.) of 100 mm x 100 mm on the basis of a y 値 of 0.090, and dried in an oven at 90 ° C for 60 seconds (prebaking). Subsequently, the entire coating film was exposed at 200 m/cm 2 (illuminance 20 mW/cm 2 ), and the exposed solution was covered with a solution of 1% 7jc of an alkali developer CDK-1 (FUJI FILM ELECTRONICS MA TE RIA LS). Apply the film and let stand for 60 seconds. After standing, spray pure water to spray off -74- 200821362 developer. Then, 'the coating film subjected to exposure and development as described above' was heat-treated (post-baked) in an oven at 220 ° C for 1 hour, and a coloring pattern (colored resin film) for color filters was formed on the glass substrate. Manufacturer color filter substrate (color filter). Comparative measurement and developability evaluation of the produced color filter substrate were carried out in the same manner as in Example 31. The results are shown in Table 6 below. [Examples 52 to 60] φ In addition to the pigment dispersion composition (B 1) of Example 51, which was replaced by the pigment dispersion compositions (B 2) to (B 10) obtained in Examples 22 to 30, In Example 5, the photocurable composition (color resist liquid) was prepared in the same manner. The colored filter substrate (color filter) was produced using the color resist liquid, and the same evaluation as in Example 31 was carried out. The results are shown in Table 6 below. [Comparative Example 1 9 to 2 4] The pigment dispersion composition (Rl 1) obtained by substituting the pigment dispersion composition Ru (R1) obtained in Example 1 of Example 31 for Comparative Examples 1 to 6 was replaced. A photocurable composition (color resist liquid) was prepared in the same manner as in Example 31 except for R 16). The colored filter substrate (color filter) was produced using the color resist liquid, and the same evaluation as in Example 31 was carried out. The results are shown in Table 4 below. [Comparative Examples 25 to 30] The pigment dispersion composition (G 1 ) obtained in Example 11 of Example 41 was replaced with the pigment dispersion composition (〇η) obtained in Comparative Examples 7 to 12 (〇1). 6) The photocurable composition (color resist liquid) was prepared in the same manner as in Example 41 except that -75 - 200821362. The colored filter substrate (color filter) was produced by using the color resist liquid. The same evaluation as in Example 41 was carried out. The results are shown in Table 5 below. [Comparative Examples 31 to 36] The pigment dispersion composition φ (B 11) obtained by substituting the pigment dispersion composition (B 1) obtained in Example 21 of Example 51 for the pigment dispersion composition φ (B 11) obtained in Comparative Example 13 to 18. A photocurable composition (color resist liquid) was prepared in the same manner as in Example 51 except for (B16). The colored filter substrate (color filter) was produced using the color resist liquid, and the same evaluation as in Example 51 was carried out. The results are shown in Table 6 below. , -76- 200821362

[表4] 紅色顏料分散組成物 對比 顯影性 實施例31 R1 1150 〇 實施例32 R2 1300 〇 實施例33 R3 1300 〇 實施例34 R4 1300 〇 實施例35 R5 1300 〇 實施例36 R6 1300 〇 實施例37 R7 1250 〇 實施例38 R8 1300 〇 實施例39 R9 1300 〇 實施例40 R10 1300 △ 比較例19 R11 1050 X 比較例20 R12 900 X 比較例21 R13 850 △ 比較例22 R14 1050 X 比較例23 R15 1050 X 比較例24 R16 1050 X -77- 200821362 [表5][Table 4] Red Pigment Dispersion Composition Comparative Development Example 31 R1 1150 〇 Example 32 R2 1300 〇 Example 33 R3 1300 〇 Example 34 R4 1300 〇 Example 35 R5 1300 〇 Example 36 R6 1300 〇 Example 37 R7 1250 〇 Example 38 R8 1300 〇 Example 39 R9 1300 〇 Example 40 R10 1300 △ Comparative Example 19 R11 1050 X Comparative Example 20 R12 900 X Comparative Example 21 R13 850 △ Comparative Example 22 R14 1050 X Comparative Example 23 R15 1050 X Comparative Example 24 R16 1050 X -77- 200821362 [Table 5]

綠色顏料分散組成物 對比 顯影性 實施例41 G1 1400 〇 實施例42 G2 1450 〇 實施例43 G3 1500 〇 實施例44 G4 1500 〇 實施例45 G5 1450 〇 實施例46 G6 1450 〇 實施例47 G7 1400 △ 實施例48 G8 1450 〇 實施例49 G9 1400 〇 實施例50 G10 1500 Δ 比較例25 G11 1200 X 比較例26 G12 1000 X 比較例27 G13 950 X 比較例28 G14 1150 X 比較例29 G15 1150 X 比較例30 G16 1150 X -78-Green Pigment Dispersion Composition Comparative Development Example 41 G1 1400 〇 Example 42 G2 1450 〇 Example 43 G3 1500 〇 Example 44 G4 1500 〇 Example 45 G5 1450 〇 Example 46 G6 1450 〇 Example 47 G7 1400 △ Example 48 G8 1450 〇 Example 49 G9 1400 〇 Example 50 G10 1500 Δ Comparative Example 25 G11 1200 X Comparative Example 26 G12 1000 X Comparative Example 27 G13 950 X Comparative Example 28 G14 1150 X Comparative Example 29 G15 1150 X Comparative Example 30 G16 1150 X -78-

'V 200821362 [表6] 藍色顏料分散組成物 對比 顯影性 實施例51 B1 1050 〇 實施例52 B2 1050 ’ 〇 實施例53 B3 1150 弋': , 〇 實施例54 B4 1100 -Λ · Ο 實施例55 B5 1100 '氣 實施例56 B6 1100 Ο ' 實施例57 B7 1000 〇 實施例58 B8 1050 〇 實施例59 B9 1050 〇. 實施例60 B10 1100 Δ 比較例31 B11 900 Δ 比較例32 B12 800 X 比較例33 B13 700 Δ 比較例34 B14 750 △ 比較例35 B15 750 Δ 比較例36 B16 750 Δ 如表4〜6所示,使用實施例的光硬化性組成物(含有本 發明的顏料分散組成物而構成)所製造的著色濾光基板(實 施例的彩色濾光片)中任一者都能夠得到高對比,顯示良好 的顯影性。相對地。比較例的著色濾光基板之對比差,又, 無法得到充分的顯影性。 【圖式簡單說明】 〇 y vv\ -79-'V 200821362 [Table 6] Blue pigment dispersion composition Comparative developability Example 51 B1 1050 〇 Example 52 B2 1050 ' 〇 Example 53 B3 1150 弋 ': , 〇 Example 54 B4 1100 - Λ · 实施 Example 55 B5 1100 'Gas Example 56 B6 1100 Ο 'Example 57 B7 1000 〇 Example 58 B8 1050 〇 Example 59 B9 1050 〇. Example 60 B10 1100 Δ Comparative Example 31 B11 900 Δ Comparative Example 32 B12 800 X Comparison Example 33 B13 700 Δ Comparative Example 34 B14 750 Δ Comparative Example 35 B15 750 Δ Comparative Example 36 B16 750 Δ As shown in Tables 4 to 6, the photocurable composition of the example (containing the pigment dispersion composition of the present invention) was used. Any of the colored filter substrates (color filters of the examples) produced by the method can obtain high contrast and exhibit good developability. relatively. The contrast of the colored filter substrate of the comparative example was poor, and sufficient developability could not be obtained. [Simple description of the diagram] 〇 y vv\ -79-

Claims (1)

200821362 十、申請專利範圍: 1. 一種顏料分散組成物,其在有機溶劑中含有顏料、及含 有來自下述通式(1)所示單體之共聚合單位聚合物’ [化學式1] 通式(1)200821362 X. Patent application scope: 1. A pigment dispersion composition containing a pigment in an organic solvent and a copolymerized unit polymer containing a monomer derived from the following formula (1) [Chemical Formula 1] (1) [在通式(1)中,R1表示氫原子、或是取代或未取代之烷 基;R2 表示伸烷基;W 表示-CO-、-C( = 0)0-、-CONH-、 -〇C( = 〇)-、或伸苯基;X表示- 0-、-S-、-C( = 〇)〇-、-C〇NH-、 _C( = 〇)S_ 、 -NHCONH- 、 _NHC( = 〇)〇· 、 -NHC( = 0)S-、 -〇C( = 〇)-、-OCONH-、或-NHC0-; Y 表示- NR3-、·0-、-S -、 或-N=,透過與Y鄰接的原子團與N原子連結而形成環狀 結構;R3表示氫原子、烷基或芳基;m及η各自獨立地 表不0或1 ]。 2. 如申請專利範圍第1項之顏料分散組成物,其中在該通 式(1)中,Υ透過鄰接的原子團與Ν原子連結而形成之環 狀結構係縮合環結構。 3. 如申請專利範圍第1或2項之顏料分散組成物,其中該 聚合物係更含有來自在末端具有乙烯性不飽和鍵之聚合 性低聚物的共聚合單位之接枝共聚物。 4. 如申請專利範圍第1或2項之顏料分散組成物,其中該 聚合物係更含有來自具有酸基之單體的共聚合單位之聚 合物。 •80- 200821362 5 ·如申請專利範圍第1項之顏料分散組成物,其中該聚合 物的酸價係10〜150毫克KOH/克。 6.如申請專利範圍第1項之顏料分散組成物,其中該顏料 係選自由C · I ·顏料黃1 3 9、C . I ·顏料黃1 5 0.、C · I.顏料綠3 6、 C.I.顏料紅177、C.I,顏料紅254、C.I.顏料藍15 : 6、及 C.I.顏料紫23所組成群組中之至少1種顏料。 7 · 一種光硬化性組成物,其含有如申請專利範圍第1項之 顏料分散組成物、光聚合性化合物、及光聚合引發劑。 、 δ·如申請專利範圍第7項之光硬化性組成物,其中更含有 鹼可溶性樹脂。 9 ·如申請專利範圍第7或8項之光硬化性組成物,其中該 光聚合引發劑係選自由三阱系化合物、咯吩二聚物類系 化合物、及肟系化合物所組成群組中之至少1種光聚合 .引發劑。 1 0.如申請專利範圍第7或8項之光硬化性組成物,係彩色 濾光片用。 1 1 · 一種彩色濾光片,具有在基板上使用如申請專利範圍第 1 0項之光硬化性組成物而構成之著色圖案。 1 2. —種彩色濾光片之製法,係包含感光性膜形成步驟及著 色圖案形成步驟,該感光性膜形成步驟係將如申請專利 範圍第1 0項之光硬化性組成物直接或透過其他的層賦 予在基板上來形成感光性膜;而該著色圖案形成步驟係 藉由在所形成的感光性膜上依次進行圖案曝光及顯影來 形成著色圖案。 200821362 七、指定代表圖: (一) 本案指定代表圖為:無。 (二) 本代表圖之元件符號簡單說明: Μ 〇 /\\\[In the formula (1), R1 represents a hydrogen atom or a substituted or unsubstituted alkyl group; R2 represents an alkylene group; and W represents -CO-, -C(=0)0-, -CONH-, - 〇C( = 〇)-, or stretch phenyl; X means - 0-, -S-, -C( = 〇)〇-, -C〇NH-, _C( = 〇)S_, -NHCONH-, _NHC ( = 〇)〇· , -NHC( = 0)S-, -〇C( = 〇)-, -OCONH-, or -NHC0-; Y means - NR3-, ·0-, -S -, or - N=, a radical structure is formed by linking an atomic group adjacent to Y to an N atom; R3 represents a hydrogen atom, an alkyl group or an aryl group; and m and η each independently represent 0 or 1]. 2. The pigment dispersion composition of claim 1, wherein in the general formula (1), the ruthenium is formed by a condensed ring structure formed by linking adjacent atoms to a ruthenium atom. 3. The pigment dispersion composition of claim 1 or 2, wherein the polymer further comprises a graft copolymer derived from a copolymerization unit of a polymerizable oligomer having an ethylenically unsaturated bond at a terminal. 4. The pigment dispersion composition of claim 1 or 2, wherein the polymer further comprises a polymer derived from a copolymerization unit of a monomer having an acid group. • 80-200821362 5 The pigment dispersion composition of claim 1, wherein the polymer has an acid value of 10 to 150 mg KOH/g. 6. The pigment dispersion composition of claim 1, wherein the pigment is selected from the group consisting of C · I · Pigment Yellow 1 3 9 , C. I · Pigment Yellow 1 5 0., C · I. Pigment Green 3 6 At least one of the group consisting of CI Pigment Red 177, CI, Pigment Red 254, CI Pigment Blue 15: 6, and CI Pigment Violet 23. A photocurable composition comprising the pigment dispersion composition of the first aspect of the patent application, a photopolymerizable compound, and a photopolymerization initiator. δ· The photocurable composition of claim 7 of the patent application, which further contains an alkali-soluble resin. 9. The photocurable composition according to claim 7 or 8, wherein the photopolymerization initiator is selected from the group consisting of a triple well compound, a spheroid dimer compound, and a lanthanoid compound. At least one photopolymerization initiator. 1 0. The photocurable composition of claim 7 or 8 is for use as a color filter. 1 1 A color filter having a colored pattern formed on a substrate using a photocurable composition as disclosed in claim 10 of the patent application. 1 2. A method for producing a color filter comprising a photosensitive film forming step and a coloring pattern forming step of directly or permeable the photocurable composition according to claim 10 of the patent application scope The other layer is provided on the substrate to form a photosensitive film; and the colored pattern forming step forms a colored pattern by sequentially performing pattern exposure and development on the formed photosensitive film. 200821362 VII. Designation of representative representatives: (1) The representative representative of the case is: None. (2) A brief description of the symbol of the representative figure: Μ 〇 /\\\ 八、本案若有化學式時,請揭示最能顯示發明特徵的化學式:8. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention:
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