WO2014088159A1 - 트리아릴메탄 염료 고분자 화합물, 이를 포함하는 컬러필터용 청색 수지 조성물 및 이를 이용한 컬러필터 - Google Patents
트리아릴메탄 염료 고분자 화합물, 이를 포함하는 컬러필터용 청색 수지 조성물 및 이를 이용한 컬러필터 Download PDFInfo
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- WO2014088159A1 WO2014088159A1 PCT/KR2013/002302 KR2013002302W WO2014088159A1 WO 2014088159 A1 WO2014088159 A1 WO 2014088159A1 KR 2013002302 W KR2013002302 W KR 2013002302W WO 2014088159 A1 WO2014088159 A1 WO 2014088159A1
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- WO
- WIPO (PCT)
- Prior art keywords
- formula
- substituted
- carbon atoms
- triarylmethane dye
- resin composition
- Prior art date
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- 0 CC(C(C=C1)=C([C@]2c(cccc3)c3C(NC(CC3)CCC3OC(C(*)=C)=O)=CC2)c(cc2)c(*)cc2N(C)*)=CC1=[N+](*)* Chemical compound CC(C(C=C1)=C([C@]2c(cccc3)c3C(NC(CC3)CCC3OC(C(*)=C)=O)=CC2)c(cc2)c(*)cc2N(C)*)=CC1=[N+](*)* 0.000 description 1
Classifications
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- 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
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
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- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
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- 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
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/103—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a diaryl- or triarylmethane dye
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic filters
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- 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
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- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic 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
- G03F7/004—Photosensitive materials
- G03F7/04—Chromates
-
- 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
- the liquid crystal display displays an image by using optical and electrical properties of the liquid crystal material.
- the liquid crystal display device has advantages such as light weight, low power, low driving voltage, and the like compared to a CRT, a plasma display panel, and the like.
- the liquid crystal display device includes a liquid crystal layer positioned between glass substrates. Light generated from the light source passes through the liquid crystal layer, and the liquid crystal layer controls light transmittance. The light passing through the liquid crystal passes through the color filter layer and implements a full color screen by additive mixing using light passing through the color filter layer.
- R 5 , R 6 and R 7 are each independently hydrogen or methyl.
- R 8 is selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms,
- the monomer corresponding to [Formula 1] may be a unit compound represented by the following [Formula 6].
- X - is trifluoromethanesulfonic acid or bistrifluoromethanesulfonimide anion
- R 10 , R 11 , R 12, and R 13 are each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms,
- R 17 is selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms,
- R 19 is selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms.
- the monomer corresponding to [Formula 4] may be a unit compound represented by the following [Formula 9].
- R 20 is selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms.
- R 21 is selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms.
- the polymer compound may have a weight average molecular weight (Mw) of 2,000-150,000.
- Blue resin composition for a color filter according to another feature of the present invention is a blue colorant; Binder resins; Reactive unsaturated compounds; Polymerization initiator; Organic solvents; And additives; It includes, wherein the blue colorant is characterized in that the triarylmethane dye polymer compound according to the present invention.
- the blue colorant is characterized in that it further comprises any one or more dyes selected from the group consisting of xanthene dyes, cyanine dyes and azapopyrine dyes.
- the blue colorant is characterized in that it further comprises any one or more pigments selected from the group consisting of a blue pigment or a purple pigment.
- the blue colorant is characterized in that 0.01% by weight to 50% by weight relative to the total weight of the blue resin composition.
- the reactive unsaturated compound may be a thermosetting monomer or oligomer; Photocurable monomers and oligomers; And it is characterized in that any one or more selected from the group consisting of a combination thereof.
- the polymerization initiator may be any one or more selected from the group consisting of a thermal polymerization initiator, a photopolymerization initiator, and a combination thereof.
- the color filter according to another feature of the present invention is prepared using the blue resin composition for color filters according to the present invention.
- the blue resin composition for color filters is prepared using the triarylmethane dye polymer compound according to the present invention, it is possible to provide a composition having an excellent effect of high brightness, high contrast ratio, heat resistance and chemical resistance.
- the blue resin composition for a color filter including the triarylmethane dye polymer compound may be manufactured in a composition exhibiting high brightness and high contrast ratio, rather than using a conventional pigment, and also compared to using a conventional triarylmethane dye. It is possible to prepare compositions with significantly improved heat and chemical resistance.
- the inventors of the present invention conducted a number of experiments to synthesize a triarylmethane dye polymer compound having excellent solubility and heat resistance and chemical resistance in an organic solvent such as propylene glycol monomethyl ether acetate (PGMEA).
- PMEA propylene glycol monomethyl ether acetate
- X - is trifluoromethanesulfonic acid or bistrifluoromethanesulfonimide anion
- R 1 , R 2 , R 3 and R 4 are each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms,
- R 5 , R 6 and R 7 are hydrogen or methyl.
- R 8 is selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms,
- R 9 is hydrogen or methyl.
- the weight average molecular weight (Mw) of the triarylmethane dye polymer compound is preferably 2,000-150,000, when the molecular weight is less than 2,000, the chemical resistance is poor, when the molecular weight exceeds 150,000, the solubility with the solvent is lowered You can.
- the weight average molecular weight (Mw) of the triarylmethane dye polymer compound is more preferably 2,000-30,000, and when it is satisfied, it shows excellent solubility, brightness, contrast ratio, heat resistance, and chemical resistance.
- the monomer unit compound corresponding to the triarylmethane dye compound structure represented by [Formula 1] may be represented by the following [Formula 6].
- X - is trifluoromethanesulfonic acid or bistrifluoromethanesulfonimide anion
- R 10 , R 11 , R 12, and R 13 are each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms,
- R 14 , R 15 and R 16 are hydrogen or methyl.
- R 19 is selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms.
- the blue dye compound including one or more other dyes or pigments optionally together with the triarylmethane dye polymer compound proposed in the present invention as the blue colorant is preferably included in an amount of 0.01% to 50% by weight based on the total weight of the blue resin composition.
- the blue dye compound is included in the composition range, it is preferable because it has excellent solubility, brightness, heat resistance, and chemical resistance to a solvent.
- a blue resin composition for a color filter was manufactured in the same manner as in Example 2-1, except that 1.9 g of the triarylmethane dye polymer compound prepared according to Synthesis Example 2 was used as the blue dye compound.
- a blue resin composition for a color filter was manufactured in the same manner as in Example 2-1, except that 1.9 g of the triarylmethane dye polymer compound prepared in Synthesis Example 3 was used as a blue dye compound.
- a blue resin composition for a color filter was manufactured in the same manner as in Example 2-1, except that 1.9 g of the triarylmethane dye polymer compound prepared according to Synthesis Example 4 was used as the blue dye compound.
- a blue resin composition for a color filter was manufactured in the same manner as in Example 2-1, except that 1.9 g of the triarylmethane dye polymer compound prepared in Synthesis Example 7 was used as the blue dye compound.
- compositions prepared according to Examples 2-1 to 2-7 and the respective compositions prepared according to Comparative Examples 1 and 2 were applied to a 0.7 mm thick organic substrate using a spin coater. After pre-bake for 150 seconds on a hot plate at 100 ° C., the wafer was exposed for 10 seconds using the exposure machines 300 W and 365. Thereafter, the composition was dried in a 220 ° C. hot air oven for 30 minutes to undergo postbake, and the respective compositions prepared according to Examples 2-1 to 2-7, Comparative Example 1, and Comparative Example 2 were applied. Specimen was produced. With each of these specimens, brightness was measured using a spectrophotometer MCPD3700, manufactured by Otsuka electronic, and contrast ratio was measured using CT-1 from Tsubosaka. The results are shown in the following [Table 2].
- Table 2 shows the measurement results of brightness, contrast ratio, heat resistance and chemical resistance according to Experimental Examples 1 to 3.
- Examples 2-1 to 2-7 there is no significant difference in terms of brightness and contrast ratio compared to Comparative Example 2, but it can be confirmed that heat resistance and chemical resistance are greatly improved.
- the triaryl methane dye polymer compound according to the present invention it was confirmed that exhibits an excellent effect than when using a conventional triaryl methane dye monomer.
- the color filter is prepared using the triarylmethane dye polymer compound according to the embodiment as a blue colorant, it was confirmed that the luminance and contrast ratio can be greatly improved as compared with the conventional pigment compound.
- the blue resin composition for color filters is prepared using the triarylmethane dye polymer compound according to the present invention, it is possible to provide a composition having an excellent effect of high brightness, high contrast ratio, heat resistance and chemical resistance.
- the blue resin composition for a color filter including the triarylmethane dye polymer compound may be manufactured in a composition exhibiting high brightness and high contrast ratio, rather than using a conventional pigment, and also compared to using a conventional triarylmethane dye. It is possible to prepare compositions with significantly improved heat and chemical resistance.
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optical Filters (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
구분 | 합성예 1 | 합성예 2 | 합성예 3 | 합성예 4 | 합성예 5 | 합성예 6 | 합성예 7 |
a) | 3.0 g | ||||||
b) | 3.0 g | ||||||
c) | 3.0 g | 3.0 g | 3.0 g | 3.0 g | |||
d) | 3.0 g | ||||||
e) | 0.96 g | 0.96 g | 0.96 g | 0.96 g | 0.60 g | ||
f) | 0.96 g | 0.96 g | 0.96 g | 0.96 g | 0.60 g | ||
g) | 0.60 g | 0.60 g | 0.60 g | 0.60 g | |||
h) | 0.96 g | ||||||
i) | 0.96 g | ||||||
j) | 0.96 g | ||||||
k) | 0.96 g | ||||||
AIBN | 0.48 g | 0.48 g | 0.48 g | 0.48 g | 0.48 g | 0.48 g | 0.48 g |
수평균분자량 | 2210 | 3343 | 3529 | 4429 | 3312 | 3738 | 2706 |
중량평균분자량 | 3435 | 7601 | 11422 | 20318 | 5330 | 10763 | 6308 |
분산도 | 1.55 | 2.27 | 3.24 | 4.59 | 1.61 | 2.88 | 2.33 |
구분 | x | y | 휘도 | 명암비 | 내열성ΔEab* | 내화학성 ΔEab* | |
PGMEA | MMP/DIGLYME | ||||||
실시예 2-1 | 0.1410 | 0.113 | 15.08 | 15600 | 1.71 | 0.29 | 1.07 |
실시예 2-2 | 0.1425 | 15.24 | 17980 | 1.38 | 0.17 | 0.67 | |
실시예 2-3 | 0.143 | 15.17 | 16803 | 1.50 | 0.24 | 0.81 | |
실시예 2-4 | 0.1397 | 15.63 | 18914 | 1.20 | 0.18 | 0.52 | |
실시예 2-5 | 0.1405 | 15.40 | 17569 | 1.16 | 0.22 | 0.81 | |
실시예 2-6 | 0.1395 | 15.51 | 19311 | 1.24 | 0.16 | 0.44 | |
실시예 2-7 | 0.1407 | 15.68 | 18128 | 1.07 | 0.18 | 0.64 | |
비교예 1 | 0.1365 | 13.70 | 11020 | 1.04 | 0.15 | 0.47 | |
비교예 2 | 0.1399 | 15.36 | 19755 | 8.73 | 25.51 | 58.67 |
Claims (15)
- 제1항에 있어서,상기 고분자 화합물은 중량평균분자량(Mw)이 2,000-150,000인 것을 특징으로 하는 트리아릴메탄 염료 고분자 화합물.
- 청색 착색제; 바인더 수지; 반응성 불포화 화합물; 중합 개시제; 유기용제; 및 첨가제;를 포함하고,상기 청색 착색제는 제1항에 따른 트리아릴메탄 염료 고분자 화합물인 것을 특징으로 하는 컬러필터용 청색 수지 조성물.
- 제9항에 있어서,상기 청색 착색제에는 크산텐 염료, 시아닌 염료 및 아자포피린 염료 중에서 선택된 어느 하나 이상의 염료를 더 포함하는 것을 특징으로 하는 컬러필터용 청색 수지 조성물.
- 제9항에 있어서,상기 청색 수지 조성물은 청색 안료 또는 보라색 안료를 더 포함하는 것을 특징으로 하는 컬러필터용 청색 수지 조성물.
- 제9항에 있어서,상기 청색 착색제는 청색 수지 조성물 총 중량에 대하여 0.01중량% 내지 50중량%인 것을 특징으로 하는 컬러필터용 청색 수지 조성물.
- 제9항에 있어서,상기 반응성 불포화 화합물은 열경화성 단량체나 올리고머; 광경화성 단량체나 올리고머; 및 이들의 조합; 중에서 선택된 어느 하나인 것을 특징으로 하는 컬러필터용 청색 수지 조성물.
- 제9항에 있어서,상기 중합 개시제는 열중합 개시제; 광중합 개시제; 및 이들의 조합;으로 이루어지는 군 중에서 선택된 어느 하나 이상인 것을 특징으로 하는 컬러필터용 청색 수지 조성물.
- 제9항에 따른 컬러필터용 청색 수지 조성물을 이용하여 제조된 컬러필터.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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US14/649,058 US9348060B2 (en) | 2012-12-03 | 2013-03-20 | Polymeric triarylmethane dye, blue resin composition including for color filter including the polymeric dye and color filter using the resin composition |
JP2015543947A JP6046831B2 (ja) | 2012-12-03 | 2013-03-20 | トリアリールメタン染料高分子化合物、それを含むカラーフィルター用青色樹脂組成物及びそれを利用したカラーフィルター |
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KR10-2012-0139155 | 2012-12-03 | ||
KR1020120139155A KR101467995B1 (ko) | 2012-12-03 | 2012-12-03 | 트리아릴메탄 염료 고분자 화합물, 이를 포함하는 컬러필터용 청색 수지 조성물 및 이를 이용한 컬러필터 |
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WO2014088159A1 true WO2014088159A1 (ko) | 2014-06-12 |
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US (1) | US9348060B2 (ko) |
JP (1) | JP6046831B2 (ko) |
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WO (1) | WO2014088159A1 (ko) |
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JP2016053153A (ja) * | 2014-07-29 | 2016-04-14 | 住友化学株式会社 | 着色硬化性樹脂組成物 |
JP2016204462A (ja) * | 2015-04-17 | 2016-12-08 | 富士フイルム株式会社 | 着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子および画像表示装置 |
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KR20190051937A (ko) | 2019-05-09 | 2019-05-15 | 제이에스알 가부시끼가이샤 | 감방사선성 조성물, 착색 조성물, 경화막, 절연막 및 그의 제조 방법, 스페이서 및 컬러 필터와 이들의 제조 방법, 그리고 액정 표시 소자 |
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JP6046831B2 (ja) | 2016-12-21 |
US20150316687A1 (en) | 2015-11-05 |
JP2016505655A (ja) | 2016-02-25 |
US9348060B2 (en) | 2016-05-24 |
KR101467995B1 (ko) | 2014-12-02 |
KR20140071146A (ko) | 2014-06-11 |
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