WO2013050431A1 - Sel pour filtre coloré, procédé de fabrication associé, et colorant le comprenant - Google Patents

Sel pour filtre coloré, procédé de fabrication associé, et colorant le comprenant Download PDF

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Publication number
WO2013050431A1
WO2013050431A1 PCT/EP2012/069553 EP2012069553W WO2013050431A1 WO 2013050431 A1 WO2013050431 A1 WO 2013050431A1 EP 2012069553 W EP2012069553 W EP 2012069553W WO 2013050431 A1 WO2013050431 A1 WO 2013050431A1
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WO
WIPO (PCT)
Prior art keywords
salt
formula
same
colorant
alkyl
Prior art date
Application number
PCT/EP2012/069553
Other languages
English (en)
Inventor
Kisuck Jung
Sangmin Han
Iljo Choi
Eunha Jeong
Original Assignee
Solvay Sa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Solvay Sa filed Critical Solvay Sa
Priority to CN201280059929.0A priority Critical patent/CN103987794A/zh
Priority to JP2014533875A priority patent/JP2014534290A/ja
Priority to KR1020147011580A priority patent/KR20140082764A/ko
Publication of WO2013050431A1 publication Critical patent/WO2013050431A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0002—Grinding; Milling with solid grinding or milling assistants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • a salt for color filter application a process for making the same, and a colorant comprising the same
  • This invention is generally directed to a salt suitable for color filter application, especially to a cyanine-xanthene salt, and processes for the preparation thereof. More specifically, the present invention is directed to the preparation of a salt comprising at least one cationic cyanine compound and at least one anionic xanthene compound, which exhibits better characteristics for color filters. Further, the present invention also relates to a display device, especially a liquid crystal display in which the foregoing salt is incorporated.
  • Color filters particularly those used in liquid crystal display (LCD) device and the like, are usually produced by first forming a pattern from a photoresist and subsequently dyeing the pattern.
  • this method is mostly
  • soluble dyes such as cyanine dye, xanthene dye and azo dye is proposed to improve solubility of the colorant for color filter.
  • US20080237553 Al discloses a colored photosensitive resin composition
  • a colored photosensitive resin composition comprising an alkali- solution resin, a photosensitive compound, a curing agent, a solvent and a cyanine colorant, in which a cyanine molecule is used as a violet colorant.
  • US20040074018 Al discloses dye mixtures consisting essentially of an azo compound such as C.I. Reactive Red 23, and a xanthene compound such as C.I. Acid Red 52, and their use in ink-jet printing and yields storage-stable and water-proof ink formulations.
  • an azo compound such as C.I. Reactive Red 23
  • a xanthene compound such as C.I. Acid Red 52
  • One of the purposes of the invention is to develop compositions for color filters exhibiting good performances including contrast ratio and brightness when used as the pigment of color filters for liquid crystal displays (LCDs).
  • LCDs liquid crystal displays
  • the inventors of the present invention have tried to resolve the problems, and discovered that the performances of the color filter pigment can be improved when a cyanine-xanthene salt is used. Further, they also discovered that if the salt is formed using an anionic xanthene compound and a cationic cyanine compound, it shows improved thermal stability, and the resultant color filter from the salt can exhibit better performances in terms of contrast ratio and brightness.
  • the present invention therefore, relates to a salt comprising, as cation, at least one cationic cyanine compound, and, as anion, at least one anionic xanthene compound.
  • dye is defined herein as a colorant that is soluble in water or other solvents. Especially, the dye has an affinity to the substrate to which it is applied.
  • pigment is defined herein as a colorant that changes the color of reflected or transmitted light as the result of wavelength- selective absorption and is not soluble in water and other solvents. Even though, both dyes and pigments appear to be colored because they absorb some wavelengths of light preferentially, in contrast with a dye, a pigment generally is insoluble, and has no affinity for the substrate.
  • salt is defined herein as materials in solid or in solution formed from an anion(s) and a cation(s).
  • the anionic xanthene compound is re resented by Formula (I) below
  • Rl, R2, R3 and R4 are same or different at each occurrence and
  • Rl, R2, R3 and R4 may be the same or different at each occurrence, preferably the same.
  • Rl, R2, R3 and R4 are advantageously independently selected from a group consisting of alkyl having 1 to 4 carbon atoms, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl and t-butyl, more preferably ethyl.
  • m is typically from 2 to 5, especially from 2 to 4, more especially 2 or 3, for instance 2.
  • the at least one SO 3 " group may be located in ortho, meta or para, advantageously in ortho or para, preferably in at least both ortho and para if at least two SO 3 " groups are present.
  • the anionic xanthene compound is represented by Formula I-l) below.
  • the xanthene compounds as represented by Formula (I) and more specifically by Formula (I-l) can be prepared by any methods known in the art.
  • Formula (I-l) can be prepared by addition of aminophenol and formyl- sulfonic acid sodium salt in p-toluene-sulfonic acid, filtering the mixture, washing and evaporation of the resultant filtrate.
  • the cationic cyanine compound is typically represented by Formula (II) below
  • - A and B are same or different at each occurrence, preferably the same, and independently selected from a group consisting of aromatic ring, heteroaromatic ring, and polyaromatic ring having 3 to 20 carbon atoms, preferably 6 to 16 carbon atoms, especially benzene or naphthalene, said group being optionally substituted by fluorinated or non-fluorinated alkyl
  • - R5 and R6 are same or different at each occurrence, especially the same, and independently selected from a group consisting of alkyl, alkoxy and hydroxyalkyl having 1 to 30 carbon atoms, preferably 2 to 20 carbon atoms, most preferably 4 to 15 carbon atoms, which may be optionally substituted by other atoms, preferably halogen, more preferably fluorine
  • - Xi, X 2 , X3 and X4 may be any kind of substituents, preferably the same or different at each occurrence, in particular the same, and independently selected from a group consist
  • Y 2 and Y 3 are same or different at each occurrence and independently selected from a group consisting of hydrogen, halogen, cyano, nitro, alkyl, and aryl groups, which may be taken together to form a 5 or 6 membered ring and
  • - n is 1 to 5, preferably 1 to 3.
  • At least one of Yi, Y2 and Y 3 of Formula (II) is cyano or halogen, preferably cyano or chlorine.
  • at least one of Xi to X 4 , R5 and R6 is an alkyl substituted by at least one fluorine atom.
  • the cationic cyanine compound is represented by any one of Formulae (II- 1) to (II-6) :
  • the cationic cyanine compound is represented by Formula (II-6) above.
  • the cyanine compounds as represented by Formula (II) and more specifically by Formulae (II- 1) to (II-6) can typically be prepared by at least three steps.
  • an indolenine compound such as 2,3,3-trimethyl indolenine is prepared.
  • a N- substituted indolium halide such as N-butyl 2,3,3-trimetyl indolium iodide is synthesized.
  • Said N-substituted indolium halide then is subjected to the third step where a cyanine compound is produced by an anion exchange reaction with an organic or inorganic anion.
  • the preparation of cyanine compounds is, for example, described in US Patent No. 6589706, the disclosures of which being incorporated herein by reference.
  • the salt of the present invention can be obtained by the following steps :
  • the anionic xanthene compound is present in the xanthene solution of step (a) in an amount of at least 1-20 %, preferably at least 1-10 %, more preferably at least 2-7 %, especially at least 5 % by weight of the solution.
  • at least a part of the anionic xanthene compound may be present in a dispersed state in the solution, the whole amount of the anionic xanthene being not in a dissolved state.
  • the solution comprising the anionic xanthene compound may be added dropwise or more rapidly to the solution comprising the cationic cyanine compound, preferably dropwise.
  • a salt containing an anionic xanthene compound and a cationic cyanine compound is typically precipitated.
  • the precipitate may be recovered by any method known in the art, for example by filtration or centrifugation. The recovered precipitate is typically washed, usually with water.
  • the weight ratio of the anionic xanthene compound to the cationic cyanine compound is typically 2:1, preferably 1.5:1, most preferably around 1:1.
  • the solvent used for dissolving the anionic xanthene compound and the cationic cyanine compound may be the same or different, most often the same.
  • any solvent known in the art may be used but water, water-miscible solvents such as alcohol, or mixtures thereof are generally used.
  • the salt of the present invention is especially suitable as a dye, in particular as a violet dye.
  • a millbase composition for a color filter may be prepared by mixing the salt of the present invention, used as a violet colorant, with at least one other dye or pigment ; and kneading the mixture.
  • Such a millbase composition can be used as such but, if necessary, it can also be used together with different types of organic or inorganic pigments, preferably organic pigments. In the case of using different types of blue organic pigments together with the millbase composition described herein, it is desirable to use said millbase composition as a main component since it leads to better contrast ratio and brightness.
  • the millbase composition may include further additives, such as a binder, a polymer-based dispersion aid, a dispersant, a liquid medium and mixtures thereof, as described in US 7368148 which is incorporated herein by reference in its entirety.
  • a solvent such as butanol
  • a dispersant such as butanol
  • a binder such as butanol
  • the milling can be conducted in at least two steps utilizing milling beads having a different size.
  • the milling is first conducted in the presence of large beads and then in the presence of small beads. After the milling step, the beads are removed by an appropriate separation means such as a glass filter, and a millbase composition is recovered.
  • the present invention is also directed to a colorant, preferably a violet colorant, comprising the salt according to the above-described invention.
  • Said colorant may further comprise at least another dye or pigment, for instance a blue pigment such as ⁇ -type copper phthalocyanine particles or a violet pigment such as PV-23.
  • a composition for color filter comprising the salt or the colorant of the present invention, as well as to a millbase composition for a color filter, comprising the salt or the colorant of the present invention and optionally any additive selected from a group consisting of a binder, a polymer- based dispersion aid, a dispersant and a liquid medium.
  • the present invention therefore also relates to a color filter comprising said colorant.
  • Such color filters may be prepared by lithographic methods, especially through the following steps: applying the millbase composition according to the present invention on a substrate, drying, exposing and developing.
  • the color filters are applicable for preparation of a liquid crystal display device, a LED display device, or a solid- state image sensing device such as a charge coupled device (CCD) or the like.
  • CCD charge coupled device
  • the present invention therefore also relates to the use of the salt of the present invention as a dye, preferably as a violet dye, and to the use of the salt or of the colorant of the present invention for preparation of color filters, and in particular for forming the blue portion of color filters.
  • the xanthene compound prepared according to Example 2 was dispersed in water so that a concentration of 5 % was reached.
  • 2640 mL of the 5 % dispersion of xanthene were added dropwise, which led to precipitation of the product.
  • the precipitate was filtered and washed with water several times, and the product was obtained.
  • the reaction yield in salt was 60 %
  • a millbase composition was prepared by dissolving a methacrylate-based dispersant (10 parts) in 70 parts of ethanol containing 6 parts of a methacrylate- based binder with heat as necessary. 3mm diameter glass beads (100 parts) and ⁇ -type copper phthalocyanine particles (10 parts), and the salt obtained in Example 3 (2 parts) were added and milling was carried out for 24 hours on a horizontal shaker to give a millbase composition. Comparative Example 1 (Preparation of a reference millbase composition comprising Pigment Violet 23)
  • a millbase composition was prepared according to an identical manner to Example 4 except that Pigment Violet 23 (PV 23) was used instead of the salt of Example 3.
  • Color filters which were fabricated using the millbase composition according to Example 4 yielded improvements in contrast ratio and brightness by approximately 20 % and 3 %, respectively, compared to those prepared in Comparative Example 1 where Pigment Violet 23 (PV 23) was used instead of the salt of the present invention, as shown in Table 1.
  • Pigment Violet 23 PV 23
  • the salt of the present invention used as violet colorant in the millbase represents improved performances compared to the Pigment Violet 23 typically used as violet pigment in the prior art.
  • the salt according to the present invention has the advantage of having improved thermal stability.
  • the salt of the present invention also allows preparation of color filters having improved performances, specifically in terms of brightness.
  • the salt of the present invention is further useful as a colorant for color filters, not only for liquid crystal displays (LCDs), but also for subtractive color generation, as for example in electro-optical systems such as charge coupled devices, plasma displays or electroluminescent displays, and also as a colorant for electronic inks ("e-inks”) or electronic paper (“e-paper”).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Optical Filters (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

La présente invention concerne un sel comprenant, comme cation, au moins un composé cyanine cationique, et, comme anion, au moins un composé xanthène anionique, ainsi que son utilisation dans les filtres colorés, par ex. pour les écrans, et son procédé de préparation. Le sel de la présente invention donne des caractéristiques améliorées, particulièrement en termes de stabilité thermique et/ou de luminosité.
PCT/EP2012/069553 2011-10-06 2012-10-03 Sel pour filtre coloré, procédé de fabrication associé, et colorant le comprenant WO2013050431A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201280059929.0A CN103987794A (zh) 2011-10-06 2012-10-03 用于滤色器应用的盐、制造该盐的方法、以及含该盐的着色剂
JP2014533875A JP2014534290A (ja) 2011-10-06 2012-10-03 カラーフィルター用途向けの塩、それの製造方法、およびそれを含む着色剤
KR1020147011580A KR20140082764A (ko) 2011-10-06 2012-10-03 컬러필터에 적용되는 염, 상기 염의 제조 방법, 및 상기 염을 포함한 착색제

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP11184165 2011-10-06
EP11184165.6 2011-10-06

Publications (1)

Publication Number Publication Date
WO2013050431A1 true WO2013050431A1 (fr) 2013-04-11

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PCT/EP2012/069553 WO2013050431A1 (fr) 2011-10-06 2012-10-03 Sel pour filtre coloré, procédé de fabrication associé, et colorant le comprenant

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JP (1) JP2014534290A (fr)
KR (1) KR20140082764A (fr)
CN (1) CN103987794A (fr)
WO (1) WO2013050431A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104345566A (zh) * 2013-08-01 2015-02-11 Jsr株式会社 着色组合物、着色固化膜和显示元件
JP2016094604A (ja) * 2014-11-11 2016-05-26 住友化学株式会社 着色硬化性樹脂組成物
US9389348B1 (en) * 2013-04-26 2016-07-12 Dai Nippon Printing Co., Ltd. Color material, color material dispersion liquid, color resin composition for color filters, color filter, liquid crystal display device and organic light-emitting display device

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI756440B (zh) * 2017-06-29 2022-03-01 日商保土谷化學工業股份有限公司 含二苯并哌喃系染料之著色組合物、彩色濾光器用著色劑及彩色濾光器
KR102027036B1 (ko) * 2017-11-28 2019-09-30 주식회사 엘지화학 착색제 조성물, 착색제 분산액, 감광성 수지 조성물, 컬러필터 및 액정 표시 장치
KR102025478B1 (ko) * 2017-11-28 2019-09-25 주식회사 엘지화학 착색제 조성물 제조방법, 이를 이용하여 제조된 착색제 조성물, 착색제 분산액, 감광성 수지 조성물, 컬러필터 및 액정 표시 장치
JP7329921B2 (ja) * 2018-12-11 2023-08-21 保土谷化学工業株式会社 アゾ化合物を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター
KR102695037B1 (ko) * 2021-01-26 2024-08-12 삼성에스디아이 주식회사 화합물, 이를 포함하는 감광성 수지 조성물, 감광성 수지막, 컬러필터 및 cmos 이미지 센서

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GB2082195A (en) * 1980-07-22 1982-03-03 Showa Kagaku Kogyo Kk Colour Salts and Optically Brightening Compositions Containing the Same
EP1118416A2 (fr) 2000-01-18 2001-07-25 Miyachi Technos Corporation Alimentation comprenant un onduleur pour assembler des éléments métalliques ou pour braser par refusion
US20030096192A1 (en) * 2001-03-28 2003-05-22 Horst Berneth Optical data carrier comprising a xanthene dye as light-absorbent compound in the information layer
US6589706B1 (en) 2000-01-28 2003-07-08 Industrial Technology Research Institute Preparation of cyanine dye for high density optical recording disk
US20040074018A1 (en) 2001-02-14 2004-04-22 Andreas Wuzik Colorant composition
DE102006022756A1 (de) * 2006-05-16 2007-11-22 Lanxess Deutschland Gmbh Optischer Datenträger enthaltend in der Informationsschicht einen Indolcyaninfarbstoff als lichtabsorbierende Verbindung
US7368148B2 (en) 2004-01-19 2008-05-06 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Fabrication process of color filters, inks, color filters, and image displays using the color filters
US20080237553A1 (en) 2007-03-28 2008-10-02 Sumitomo Chemical Company, Limited Colored photosensitive resin composition, and color filter array and solid-state image pickup device using the same

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JPS5725364A (en) * 1980-07-22 1982-02-10 Showa Kagaku Kogyo Kk Dyestuff salt
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JP2002014222A (ja) * 2000-06-30 2002-01-18 Sumitomo Chem Co Ltd 青色フィルタ層を有する色フィルタアレイおよびその製造方法
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Publication number Priority date Publication date Assignee Title
GB2082195A (en) * 1980-07-22 1982-03-03 Showa Kagaku Kogyo Kk Colour Salts and Optically Brightening Compositions Containing the Same
EP1118416A2 (fr) 2000-01-18 2001-07-25 Miyachi Technos Corporation Alimentation comprenant un onduleur pour assembler des éléments métalliques ou pour braser par refusion
US6589706B1 (en) 2000-01-28 2003-07-08 Industrial Technology Research Institute Preparation of cyanine dye for high density optical recording disk
US20040074018A1 (en) 2001-02-14 2004-04-22 Andreas Wuzik Colorant composition
US20030096192A1 (en) * 2001-03-28 2003-05-22 Horst Berneth Optical data carrier comprising a xanthene dye as light-absorbent compound in the information layer
US7368148B2 (en) 2004-01-19 2008-05-06 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Fabrication process of color filters, inks, color filters, and image displays using the color filters
DE102006022756A1 (de) * 2006-05-16 2007-11-22 Lanxess Deutschland Gmbh Optischer Datenträger enthaltend in der Informationsschicht einen Indolcyaninfarbstoff als lichtabsorbierende Verbindung
US20080237553A1 (en) 2007-03-28 2008-10-02 Sumitomo Chemical Company, Limited Colored photosensitive resin composition, and color filter array and solid-state image pickup device using the same

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9389348B1 (en) * 2013-04-26 2016-07-12 Dai Nippon Printing Co., Ltd. Color material, color material dispersion liquid, color resin composition for color filters, color filter, liquid crystal display device and organic light-emitting display device
CN104345566A (zh) * 2013-08-01 2015-02-11 Jsr株式会社 着色组合物、着色固化膜和显示元件
JP2015044982A (ja) * 2013-08-01 2015-03-12 Jsr株式会社 着色組成物、着色硬化膜及び表示素子
JP2016094604A (ja) * 2014-11-11 2016-05-26 住友化学株式会社 着色硬化性樹脂組成物

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KR20140082764A (ko) 2014-07-02
JP2014534290A (ja) 2014-12-18
CN103987794A (zh) 2014-08-13

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