KR102589407B1 - triazine derivatives having a triazine group, pigment dispersing aid containing the same and pigment dispersion containing the same - Google Patents
triazine derivatives having a triazine group, pigment dispersing aid containing the same and pigment dispersion containing the same Download PDFInfo
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- KR102589407B1 KR102589407B1 KR1020160060073A KR20160060073A KR102589407B1 KR 102589407 B1 KR102589407 B1 KR 102589407B1 KR 1020160060073 A KR1020160060073 A KR 1020160060073A KR 20160060073 A KR20160060073 A KR 20160060073A KR 102589407 B1 KR102589407 B1 KR 102589407B1
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- South Korea
- Prior art keywords
- group
- pigment
- integer
- alkyl
- pigment dispersion
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- 239000000049 pigment Substances 0.000 title claims abstract description 224
- 239000006185 dispersion Substances 0.000 title claims abstract description 111
- 150000003918 triazines Chemical class 0.000 title claims abstract description 53
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title description 12
- 239000011342 resin composition Substances 0.000 claims abstract description 31
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 70
- 125000005843 halogen group Chemical group 0.000 claims description 58
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 239000002270 dispersing agent Substances 0.000 claims description 20
- 239000012756 surface treatment agent Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000006654 (C3-C12) heteroaryl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000003860 storage Methods 0.000 abstract description 13
- 230000003287 optical effect Effects 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 22
- -1 triazine compound Chemical class 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 19
- 125000000524 functional group Chemical group 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
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- 238000000034 method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
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- 125000001424 substituent group Chemical group 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
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- 230000002378 acidificating effect Effects 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 239000012860 organic pigment Substances 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- 239000001054 red pigment Substances 0.000 description 6
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- 230000002776 aggregation Effects 0.000 description 5
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- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 5
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 4
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 4
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- 239000001056 green pigment Substances 0.000 description 4
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- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 3
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- 150000004056 anthraquinones Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
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- 239000000975 dye Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
- 230000019612 pigmentation Effects 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 239000011164 primary particle Substances 0.000 description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 3
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
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- IPHJYJHJDIGARM-UHFFFAOYSA-M copper phthalocyaninesulfonic acid, dioctadecyldimethylammonium salt Chemical compound [Cu+2].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC.C=1C(S(=O)(=O)[O-])=CC=C(C(=NC2=NC(C3=CC=CC=C32)=N2)[N-]3)C=1C3=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 IPHJYJHJDIGARM-UHFFFAOYSA-M 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 235000019988 mead Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CTIQLGJVGNGFEW-UHFFFAOYSA-L naphthol yellow S Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 CTIQLGJVGNGFEW-UHFFFAOYSA-L 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/08—Treatment with low-molecular-weight non-polymer organic 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
-
- 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
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- Chemical & Material Sciences (AREA)
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Optical Filters (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
본 발명은 트리아진 유도체, 이를 포함하는 안료 분산 조제 및 이를 포함하는 안료 분산액에 관한 것으로, 본 발명의 트리아진 유도체는 내열성이 높고, 분산성이 우수하여 이를 포함하는 안료 분산액의 분산성 및 저장안정성을 향상시킨다. 따라서 본 발명의 안료 분산액을 채용한 착색 감광성 수지 조성물은 휘도 및 콘트라스트 등의 우수한 광학적 특성을 가진다.The present invention relates to a triazine derivative, a pigment dispersion aid containing the same, and a pigment dispersion containing the same. The triazine derivative of the present invention has high heat resistance and excellent dispersibility, thereby improving the dispersibility and storage stability of the pigment dispersion containing the same. improves Therefore, the colored photosensitive resin composition employing the pigment dispersion of the present invention has excellent optical properties such as brightness and contrast.
Description
본 발명은 트리아진 유도체, 이를 포함하는 안료 분산 조제 및 이를 포함하는 안료 분산액에 관한 것으로, 보다 상세하게는 안료와 친화력 및 내열성이 높아 분산성 및 저장안정성이 우수한 트리아진 유도체, 이를 포함하는 안료 분산 조제, 안료 분산 조제를 포함하는 안료 분산액 및 안료 분산액을 포함하는 착색 감광성 수지 조성물에 관한 것이다.The present invention relates to a triazine derivative, a pigment dispersion aid containing the same, and a pigment dispersion containing the same. More specifically, a triazine derivative having excellent dispersibility and storage stability due to high affinity and heat resistance for the pigment, and a pigment dispersion containing the same. It relates to an auxiliary agent, a pigment dispersion liquid containing a pigment dispersion auxiliary agent, and a colored photosensitive resin composition containing the pigment dispersion liquid.
액정 표시 장치에 사용되는 칼라 필터는 삼원색, 즉, 적(red), 녹(green) 및 청(blue)의 패턴을 유리 기판에 형성하여 제조한다. Color filters used in liquid crystal display devices are manufactured by forming patterns of three primary colors, that is, red, green, and blue, on a glass substrate.
칼라 패턴(pattern)을 제조하는 공정은 각 칼라 픽셀에 해당하는 착색제를 함유하는 감광성 착색 조성물(color resist)을 기판상에 균일하게 도포하는 단계, 도포된 조성물을 가열-건조하여 필름을 형성하는 단계, 건조된 필름을 원하는 형상의 마스크(mask)를 이용하여 선택 노광한 후 현상하는 단계 및 현상된 필름을 가열하여 경화하는 단계로 구성된다. The process of manufacturing a color pattern includes uniformly applying a photosensitive coloring composition (color resist) containing a colorant corresponding to each color pixel on a substrate, and heating and drying the applied composition to form a film. It consists of selectively exposing the dried film to light using a mask of a desired shape and then developing it, and heating and curing the developed film.
이러한 공정에 사용되는 감광성 수지 조성물의 착색제는 주로 안료를 사용하는 것이 일반적이다. It is common to mainly use pigments as colorants for photosensitive resin compositions used in these processes.
한편 최근 디스플레이 기술혁신의 흐름에 따라, 액정 표시 장치에 대해 디스플레이의 전력을 절약하기위해 고 투과(휘도), 고 콘트라스트의 특성을 가지는 안료 분산액이 요구되고 있으며, 또한 칼라영역(Color gamut)을 확장하기 위하여 고색재현율 달성을 하는 것을 목표로 하고 있다. Meanwhile, according to the recent trend of display technology innovation, pigment dispersions with high transmission (brightness) and high contrast characteristics are required to save display power for liquid crystal display devices, and also expand the color gamut. In order to achieve this, the goal is to achieve high color reproduction rate.
이러한 목표를 달성하기위해서는 안료의 농도가 높아야하나, 안료의 고 농도화는 안료 분산액 자체의 저장 안정성 및 레지스트화하였을 때에도, 저장 안정성 및 패턴의 공정성을 저하시키기 때문에, 높은 수준의 안료 분산액이 요구된다.To achieve this goal, the concentration of the pigment must be high, but a high concentration of the pigment reduces the storage stability of the pigment dispersion itself and the fairness of the pattern even when turned into a resist, so a high level of pigment dispersion is required. .
안료 분산액은 안료, 분산제, 수지 이외에, 안료 표면을 안정화 시키는 안료 분산 조제가 사용된다. 안료 분산 조제는 안료 표면을 안정화 하여, 안료 분산액의 저장성 및 안료의 승화성을 방지할 수 있으며, 또한 안료 분산 조제를 안료 표면 처리 가공 시 적용하여, 안료 표면을 보다 안정화시켜, 안료를 매우 효율적으로 분산시킬 수 있다.Pigment dispersions include pigments, dispersants, and resins, as well as pigment dispersion aids that stabilize the pigment surface. The pigment dispersion aid stabilizes the pigment surface, preventing the storage of the pigment dispersion and the sublimation of the pigment. Additionally, the pigment dispersion aid can be applied during pigment surface treatment to further stabilize the pigment surface, making the pigment very efficient. It can be dispersed.
그러나, 기존 안료 분산 조제는 대부분 안료와 같은 모체 골격에 치환기를 변경한 것을 적용함으로써, 분자 전체로서 안료와 상이한 구조를 가져, 안료와 기존 안료 분산 조제의 색 스펙트럼이 변화하여, 안료 분산액의 색 특성이 소폭 저하된다. 그 결과, 디스플레이에 표시되는 화상의 휘도가 저하되어 저전력을 목표로 하는 현 디스플레이의 개발 목표에 부합되지 않는다.However, most existing pigment dispersion aids apply substituent changes to the same matrix skeleton as the pigment, so that the molecule as a whole has a different structure from the pigment, and the color spectrum of the pigment and the existing pigment dispersion aid changes, resulting in the color characteristics of the pigment dispersion. This decreases slightly. As a result, the luminance of the image displayed on the display is lowered, which does not meet the current display development goal of low power consumption.
종래부터, 트리아진 고리를 모골격으로 하는 안료 분산제나 분산 조제가 공지되어 있으나, 공지된 구조에서는 안료 표면 처리제로써의 역할로 제한되고 있어 여전히 향상된 특성을 가지는 안료 분산 조제가 요구된다.Conventionally, pigment dispersants or dispersion aids using a triazine ring as the parent skeleton are known, but the known structure is limited to the role of a pigment surface treatment agent, and a pigment dispersion aid with improved properties is still required.
본 발명은 분산성 및 저장안정성이 우수하여 고농도에서도 고휘도의 발색이 가능한 트리아진 화합물을 제공한다.The present invention provides a triazine compound that has excellent dispersibility and storage stability, enabling high-brightness color development even at high concentrations.
또한 본 발명은 본 발명의 트리아진 화합물을 포함하는 안료 분산 조제 및 안료 표면처리제를 제공한다.Additionally, the present invention provides a pigment dispersion aid and a pigment surface treatment agent containing the triazine compound of the present invention.
또한 본 발명은 본 발명의 안료 분산 조제를 포함하는 안료 분산액을 제공한다.The present invention also provides a pigment dispersion liquid containing the pigment dispersion aid of the present invention.
또한 본 발명은 본 발명의 안료 분산액을 포함하는 착색 감광성 수지 조성물을 제공한다.The present invention also provides a colored photosensitive resin composition containing the pigment dispersion of the present invention.
본 발명은 안료와 친화력이 높아 분산성이 우수함으로써 안료 본연의 스펙트럼에 영향을 주지 않는, 분산 조제 및 안료 표면처리제로 유용한 트리아진 유도체를 제공한다.The present invention provides a triazine derivative useful as a dispersing aid and pigment surface treatment agent that has high affinity for pigments and has excellent dispersibility, thereby not affecting the original spectrum of the pigment.
본 발명의 트리아진 유도체는 하기 화학식 1로 표시된다.The triazine derivative of the present invention is represented by the following formula (1).
[화학식 1][Formula 1]
(상기 화학식 1에서,(In Formula 1 above,
X1 및 X2는 서로 독립적으로 -NH-, -O-, -CONH-, -SO2-, -SO2NH-, -CH2NH-, -CH2- 또는 -CH2NHCOCH2NH-이며; X 1 and _ _ _ _ _ and;
Ar1은 Cl, OH, (C6-C12)아릴기 또는 (C3-C12)헤테로아릴기이며; Ar 1 is Cl, OH, (C6-C12)aryl group or (C3-C12)heteroaryl group;
R1 및 R2는 서로 독립적으로 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, -SO2N(R11)(R12) 또는 -CON(R13)(R14)이며, R11 내지 R14는 서로 독립적으로 수소, (C1-C5)알킬 또는 (C6-C12)아릴기이며;R 1 and R 2 are independently of each other halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group. , (C6-C12) aryl group, -SO 2 N(R 11 )(R 12 ) or -CON(R 13 )(R 14 ), and R 11 to R 14 are independently hydrogen, (C1-C5) It is an alkyl or (C6-C12)aryl group;
Z는 CR3 또는 N이며, R3은 수소, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;Z is CR 3 or N, and R 3 is hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6-C12) It is an aryl group;
a는 0 또는 1 내지 5의 정수이며, b는 1 내지 5의 정수로, a+b≤5이며, a 및 b가 2이상인 경우 R1은 서로 상이하거나 동일할 수 있으며;a is 0 or an integer from 1 to 5, b is an integer from 1 to 5, and a+b≤5, and when a and b are 2 or more, R 1 may be different from or the same as each other;
c는 0 또는 1 내지 2의 정수로 c가 2이상인 경우 R2는 서로 상이하거나 동일할 수 있으며;c is 0 or an integer from 1 to 2, and when c is 2 or more, R 2 may be different from or the same as each other;
상기 Ar1의 아릴기 또는 헤테로아릴기는 아미노기, 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, SO2N(R11)(R12) 및 -CON(R13)(R14)에서 선택되는 어느 하나이상으로 치환될 수 있다.)The aryl group or heteroaryl group of Ar 1 is amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) It may be substituted with one or more selected from alkoxycarbonyl group, (C6-C12)aryl group, SO 2 N(R 11 )(R 12 ) and -CON(R 13 )(R 14 ).
바람직하게 본 발명의 일 실시예에 따른 상기 화학식 1에서 R1 및 R2는 서로 독립적으로 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;Preferably, in Formula 1 according to an embodiment of the present invention, R 1 and R 2 are independently selected from a halogen group, a nitro group, a carboxylic acid group, a (C1-C5) alkyl group, a (C1-C5) alkoxy group, or halo ( C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6-C12) aryl group;
X1 및 X2는 서로 독립적으로 -NH-, -SO2-, -SO2NH- 또는 -CH2NH-이며;X 1 and X 2 are independently -NH-, -SO 2 -, -SO 2 NH- or -CH 2 NH-;
Ar1은 (C6-C12)아릴기 또는 (C3-C12)헤테로아릴기이며;Ar 1 is a (C6-C12)aryl group or (C3-C12)heteroaryl group;
Z는 N일 수 있다.Z may be N.
본 발명의 일 실시예에 따른 상기 화학식 1에서 Ar1은 하기 구조식에서 선택될 수 있다.In Formula 1 according to an embodiment of the present invention, Ar 1 may be selected from the following structural formula.
(상기 구조식에서, R21 내지 R27은 서로 독립적으로, 아미노기, 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, -SO2N(R11)(R12) 또는 -CON(R13)(R14) 이며, R11 내지 R14는 서로 독립적으로 수소, (C1-C5)알킬 또는 (C6-C12)아릴기이며; (In the above structural formula, R 21 to R 27 are independently of each other amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (C6-C12) aryl group, -SO 2 N(R 11 )(R 12 ) or -CON(R 13 )(R 14 ), and R 11 to R 14 are independent of each other It is hydrogen, (C1-C5)alkyl or (C6-C12)aryl group;
D1 내지 D4는 서로 독립적으로 CR15R16 또는N이며, R15 및 R16은 서로 독립적으로 수소, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;D 1 to D 4 are each independently CR 15 R 16 or N, and R 15 and R 16 are independently hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, or halo (C1-C5) alkyl group. , (C1-C5)alkoxycarbonyl group or (C6-C12)aryl group;
D5는 CR17 또는 N이며, R17은 수소, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;D 5 is CR 17 or N, and R 17 is hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6-C12) ) is an aryl group;
d는 0 또는 1 내지 3의 정수이며, e는 0 또는 1 내지 6의 정수이며, f 는 0 또는 1 내지 4의 정수로, g는 0 또는 1 내지 2의 정수이며, h는 0 또는 1 내지 7의 정수이며, d, e, f, g 및 h가 2이상의 정수인 경우 각 R21, R22 R24, R26 및 R27은 서로 동일하거나 상이할 수 있다.)d is 0 or an integer from 1 to 3, e is 0 or an integer from 1 to 6, f is 0 or an integer from 1 to 4, g is 0 or an integer from 1 to 2, h is 0 or an integer from 1 to 2 It is an integer of 7, and when d, e, f, g and h are integers of 2 or more, each of R 21 , R 22 R 24 , R 26 and R 27 may be the same or different from each other.)
바람직하게 본 발명의 일 실시예에 따른 상기 화학식 1은 하기 화학식 2로 표시될 수 있다.Preferably, Formula 1 according to an embodiment of the present invention may be represented by Formula 2 below.
[화학식 2][Formula 2]
[상기 화학식 2에서,[In Formula 2 above,
X1 및 X2는 -NH-, -O-, -CONH-, -SO2-, -SO2NH-, -CH2NH-, -CH2- 또는 -CH2NHCOCH2NH-이며;X 1 and X 2 are -NH-, -O-, -CONH-, -SO 2 -, -SO 2 NH-, -CH 2 NH-, -CH 2 - or -CH 2 NHCOCH 2 NH-;
R1 은 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, -SO2N(R11)(R12) 또는 -CON(R13)(R14)이며, R11 내지 R14는 서로 독립적으로 수소, (C1-C5)알킬 또는 (C6-C12)아릴기이며;R 1 is a halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (C6-C12) Aryl group, -SO 2 N(R 11 )(R 12 ) or -CON(R 13 )(R 14 ), and R 11 to R 14 are independently hydrogen, (C1-C5)alkyl, or (C6-C12). ) is an aryl group;
a 는 서로 독립적으로 0 또는 1 내지 5의 정수이며, b는 1 내지 5의 정수로, a+b≤5이며, a 및 b가 2이상인 경우 R1은 서로 상이하거나 동일할 수 있으며;a is independently 0 or an integer from 1 to 5, b is an integer from 1 to 5, and a+b≤5, and when a and b are 2 or more, R 1 may be different from or the same as each other;
Ar1은 , 또는 이며;Ar 1 is , or and;
R21 내지 R22는 서로 독립적으로, 아미노기, 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, -SO2N(R11)(R12) 또는 -CON(R13)(R14) 이며, R11 내지 R14는 서로 독립적으로 수소, (C1-C5)알킬 또는 (C6-C12)아릴기이며;R 21 to R 22 are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) An alkoxycarbonyl group, (C6-C12)aryl group, -SO 2 N(R 11 )(R 12 ) or -CON(R 13 )(R 14 ), and R 11 to R 14 are independently hydrogen, (C1) -C5) alkyl or (C6-C12) aryl group;
D1은 CR15R16 또는 N이며, R15 및 R16은 서로 독립적으로 수소, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며; D 1 is CR 15 R 16 or N, and R 15 and R 16 are independently hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) It is an alkoxycarbonyl group or (C6-C12)aryl group;
d는 0 또는 1 내지 3의 정수이며, e는 0 또는 1 내지 6의 정수이며, h는 0 또는 1 내지 7의 정수이며, d, e 및 f가 2이상의 정수인 경우 각 R21, R22 및 R27은 서로 동일하거나 상이할 수 있다.)d is 0 or an integer of 1 to 3, e is 0 or an integer of 1 to 6, h is 0 or an integer of 1 to 7, and when d, e and f are integers of 2 or more, R 21 , R 22 and R 27 may be the same or different from each other.)
바람직하게 본 발명의 일 실시예에 따른 상기 화학식 2에서 X1 및 X2는 -NH-이며;Preferably, in Formula 2 according to an embodiment of the present invention, X 1 and X 2 are -NH-;
R1은 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;R 1 is a halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6-C12) It is an aryl group;
a는 0 또는 1 내지 5의 정수이며, b는 1 내지 5의 정수로, a+b≤5이며, a가 2이상인 경우 R1은 서로 상이하거나 동일할 수 있으며;a is 0 or an integer from 1 to 5, b is an integer from 1 to 5, and a+b≤5, and when a is 2 or more, R 1 may be different from or the same as each other;
Ar1은 , 또는 이며;Ar 1 is , or and;
R21 내지 R22 및 R27은 서로 독립적으로, 아미노기, 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며; R 21 to R 22 and R 27 are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1) -C5) alkoxycarbonyl group or (C6-C12) aryl group;
D1은 N이며; D 1 is N;
d는 0 또는 1 내지 3의 정수이며, e는 0 또는 1 내지 6의 정수이며, h는 0 또는 1 내지 7의 정수이며, d, e 및 h가 2이상의 정수인 경우 각 R21, R22 및 R27은 서로 동일하거나 상이할 수 있다.)d is 0 or an integer of 1 to 3, e is 0 or an integer of 1 to 6, h is 0 or an integer of 1 to 7, and when d, e and h are integers of 2 or more, R 21 , R 22 and R 27 may be the same or different from each other.)
또한 본 발명은 본 발명의 트리아진 유도체를 포함하는 안료 분산 조제를 제공한다.The present invention also provides a pigment dispersion aid containing the triazine derivative of the present invention.
또한 본 발명은 본 발명의 트리아진 유도체를 포함하는 안료 표면처리제를 제공한다.The present invention also provides a pigment surface treatment agent containing the triazine derivative of the present invention.
또한 본 발명은 안료 분산 조제, 안료, 안료 분산제 및 용제를 포함하는 안료 분산액을 제공한다.The present invention also provides a pigment dispersion liquid containing a pigment dispersion aid, a pigment, a pigment dispersant, and a solvent.
본 발명의 일 실시예에 따른 안료 분산액의 안료는 평균입자지름이 10 내지 150nm일 수 있으며, 안료 분산제는 고형분으로 상기 안료 100중량부에 대하여, 10 내지 60중량부이며, 상기 안료 분산 조제는 안료 100중량부에 대하여 1 내지 25중량부로 포함될 수 있다.The pigment of the pigment dispersion according to an embodiment of the present invention may have an average particle diameter of 10 to 150 nm, the pigment dispersant is 10 to 60 parts by weight in solid content based on 100 parts by weight of the pigment, and the pigment dispersion aid is a pigment. It may be included in an amount of 1 to 25 parts by weight per 100 parts by weight.
또한 본 발명은 본 발명의 안료 분산액 및 감광성 화합물을 포함하는 착색 감광성 수지 조성물을 제공한다.The present invention also provides a colored photosensitive resin composition comprising the pigment dispersion of the present invention and a photosensitive compound.
본 발명의 트리아진 유도체는 안료와 친화력이 높은 작용기를 가짐으로써 안료의 표면을 효과적으로 보호하여 안료 입자의 손상을 최소화하여 분산성이 우수하다.The triazine derivative of the present invention has a functional group with high affinity for the pigment, thereby effectively protecting the surface of the pigment, minimizing damage to the pigment particles, and providing excellent dispersibility.
또한 본 발명의 트리아진 유도체는 안료 표면처리제로 사용되어 조제안료를 안료화할 수 있다.Additionally, the triazine derivative of the present invention can be used as a pigment surface treatment agent to pigment a crude pigment.
따라서 본 발명의 트리아진 유도체를 포함하는 안료 분산액은 안료의 응집을 억제하는 능력이 탁월하고, 내열성이 높아 저장안정성이 우수하다.Therefore, the pigment dispersion containing the triazine derivative of the present invention has excellent ability to suppress pigment aggregation and has high heat resistance and excellent storage stability.
더불어 본 발명의 안료 분산액을 채용한 착색 감광성 수지 조성물은 고휘도 및 고색선명도를 가지며, 고농도에서도 분산성이 우수하여 저전력 표시장치의 구현이 가능하다.In addition, the colored photosensitive resin composition employing the pigment dispersion of the present invention has high brightness and high color clarity, and has excellent dispersibility even at high concentrations, making it possible to implement a low-power display device.
본 발명은 안료 분산 조제 또는 안료 표면처리제에 사용되어 분산성 및 저장안정성을 향상시키고 안료 표면을 안정화시켜 이를 채용한 디스플레이 등의 휘도 및 색선명도를 향상시키는 트리아진 유도체를 제공하는 것으로, 본 발명의 트리아진 유도체는 하기 화학식 1로 표시된다.The present invention provides a triazine derivative that is used in a pigment dispersion aid or pigment surface treatment agent to improve dispersibility and storage stability and stabilize the pigment surface to improve luminance and color vividness of displays employing the same. Triazine derivatives are represented by the following formula (1).
[화학식 1][Formula 1]
(상기 화학식 1에서,(In Formula 1 above,
X1 및 X2는 서로 독립적으로 -NH-, -O-, -CONH-, -SO2-, -SO2NH-, -CH2NH-, -CH2- 또는 -CH2NHCOCH2NH-이며; X 1 and _ _ _ _ _ and;
Ar1은 Cl, OH, (C6-C12)아릴기 또는 (C3-C12)헤테로아릴기이며; Ar 1 is Cl, OH, (C6-C12)aryl group or (C3-C12)heteroaryl group;
R1 및 R2는 서로 독립적으로 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, -SO2N(R11)(R12) 또는 -CON(R13)(R14)이며, R11 내지 R14는 서로 독립적으로 수소, (C1-C5)알킬 또는 (C6-C12)아릴기이며;R 1 and R 2 are independently of each other halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group. , (C6-C12) aryl group, -SO 2 N(R 11 )(R 12 ) or -CON(R 13 )(R 14 ), and R 11 to R 14 are independently hydrogen, (C1-C5) It is an alkyl or (C6-C12)aryl group;
Z는 CR3 또는 N이며, R3은 수소, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;Z is CR 3 or N, and R 3 is hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6-C12) It is an aryl group;
a는 0 또는 1 내지 5의 정수이며, b는 1 내지 5의 정수로, a+b≤5이며, a 및 b가 2이상인 경우 R1은 서로 상이하거나 동일할 수 있으며;a is 0 or an integer from 1 to 5, b is an integer from 1 to 5, and a+b≤5, and when a and b are 2 or more, R 1 may be different from or the same as each other;
c는 0 또는 1 내지 2의 정수로 c가 2이상인 경우 R2는 서로 상이하거나 동일할 수 있으며;c is 0 or an integer from 1 to 2, and when c is 2 or more, R 2 may be different from or the same as each other;
상기 Ar1의 아릴기 또는 헤테로아릴기는 아미노기, 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, SO2N(R11)(R12) 및 -CON(R13)(R14)에서 선택되는 어느 하나이상으로 치환될 수 있다.)The aryl group or heteroaryl group of Ar 1 is amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) It may be substituted with one or more selected from alkoxycarbonyl group, (C6-C12)aryl group, SO 2 N(R 11 )(R 12 ) and -CON(R 13 )(R 14 ).
본 발명의 트리아진 유도체는 내열성이 높아 저장안정성이 높으며, 안료의 표면의 여러 가지 기능기와 결합하여 분산성을 획기적으로 높여 이를 채용한 컬러필터 등의 디스플레이의 안료에 적용하였을 경우 우수한 휘도 및 색선명도를 가진다.The triazine derivative of the present invention has high heat resistance and storage stability, and combines with various functional groups on the surface of the pigment to dramatically increase dispersibility, resulting in excellent brightness and color clarity when applied to pigments for displays such as color filters using it. has
구체적으로 본 발명의 트리아진 유도체는 트리아진 골격에 안료와 친화력이 우수한 작용기인 트리아진 유도체 및 피리미딘 유도체를 치환기로 도입함으로써 안료 표면처리제로 사용할 시 안료 표면의 여러 가지 기능기와 결합하거나, 안료 분산 조제로 사용할 시 다양한 분산제 및 분산용 수지등과 결합력을 향상시켜 분산성을 현저하게 향상시킨다.Specifically, the triazine derivative of the present invention introduces triazine derivatives and pyrimidine derivatives, which are functional groups with excellent affinity for pigments, into the triazine skeleton as substituents, so that when used as a pigment surface treatment agent, it binds to various functional groups on the surface of the pigment or disperses the pigment. When used as an adjuvant, it significantly improves dispersibility by improving the bonding strength with various dispersants and dispersing resins.
종래의 안료 분산 조제로 사용된 트라아진 골격의 화합물과 달리 본 발명의 트리아진 유도체는 분산제 및 분산용 수지등과 결합력을 향상시킬 수 있는 산성기 및 안료와 친화력이 높아 고농도의 안료에서도 안료의 재응집을 억제하여 분산성을 높이는 트리아진 유도체 및 피리미딘 유도체를 치환기로 도입함으로써 이를 안료 분산 조제 또는 안료 표면처리제로 포함하는 안료 분산액을 채용한 착색 감광성 수지 조성물은 고휘도, 고콘트라스 값 및 저전력을 가진다.Unlike the compounds of the triazine skeleton used as conventional pigment dispersion aids, the triazine derivatives of the present invention have high affinity with acidic groups and pigments that can improve the bonding power with dispersants and dispersing resins, so they can be used as pigment remnants even at high concentrations. A colored photosensitive resin composition employing a pigment dispersion solution containing triazine derivatives and pyrimidine derivatives as a pigment dispersion aid or pigment surface treatment agent by introducing triazine derivatives and pyrimidine derivatives as substituents to suppress aggregation and increase dispersibility has high brightness, high contrast value, and low power. .
보다 구체적으로 본 발명의 트리아진 유도체는 안료, 분산제 및 분산성 수지등과 긴밀하게 결합가능한 치환기인 산성기 및 트라아진 유도체 또는 피리미딘 유도체를 작용기로 도입함으로써 안료 표면 처리제로 사용시 조제안료를 미세안료로 용이하게 안료화시켜 미세안료의 재응집을 억제하며, 안료 분산 조제로 사용시에는 안료의 다양한 작용기와 결합하여 안료 표면을 보호할 수 있고, 분산제 및 분산성 수지 등과 결합하여 분산성을 획기적으로 높일 수 있다.More specifically, the triazine derivative of the present invention is used as a pigment surface treatment agent by introducing an acidic group, which is a substituent that can be closely bonded to pigments, dispersants, dispersible resins, etc., and a triazine derivative or pyrimidine derivative as a functional group, thereby converting the crude pigment into a fine pigment. It suppresses the re-agglomeration of fine pigments by easily converting them into pigments, and when used as a pigment dispersion aid, it can protect the pigment surface by combining with various functional groups of the pigment, and can dramatically increase dispersibility by combining with dispersants and dispersing resins. You can.
바람직하게 본 발명의 일 실시예에 따른 상기 화학식 1에서 R1 및 R2는 서로 독립적으로 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;Preferably, in Formula 1 according to an embodiment of the present invention, R 1 and R 2 are independently selected from a halogen group, a nitro group, a carboxylic acid group, a (C1-C5) alkyl group, a (C1-C5) alkoxy group, or halo ( C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6-C12) aryl group;
X1 및 X2는 서로 독립적으로 -NH-, -SO2-, -SO2NH- 또는 -CH2NH-이며;X 1 and X 2 are independently -NH-, -SO 2 -, -SO 2 NH- or -CH 2 NH-;
Ar1은 (C6-C12)아릴기 또는 (C3-C12)헤테로아릴기이며;Ar 1 is a (C6-C12)aryl group or (C3-C12)heteroaryl group;
Z는 N일 수 있다.Z may be N.
바람직하게 화학식 1에서 Ar1은 하기 구조식에서 선택될 수 있으나, 이에 한정이 있는 것은 아니다.Preferably, Ar 1 in Formula 1 may be selected from the following structural formula, but is not limited thereto.
(상기 구조식에서, R21 내지 R27은 서로 독립적으로, 아미노기, 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, -SO2N(R11)(R12) 또는 -CON(R13)(R14) 이며, R11 내지 R14는 서로 독립적으로 수소, (C1-C5)알킬 또는 (C6-C12)아릴기이며; (In the above structural formula, R 21 to R 27 are independently of each other amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (C6-C12) aryl group, -SO 2 N(R 11 )(R 12 ) or -CON(R 13 )(R 14 ), and R 11 to R 14 are independent of each other It is hydrogen, (C1-C5)alkyl or (C6-C12)aryl group;
D1 내지 D4는 서로 독립적으로 CR15R16 또는N이며, R15 및 R16은 서로 독립적으로 수소, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;D 1 to D 4 are each independently CR 15 R 16 or N, and R 15 and R 16 are independently hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, or halo (C1-C5) alkyl group. , (C1-C5)alkoxycarbonyl group or (C6-C12)aryl group;
D5는 CR17 또는N이며, R17은 수소, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;D 5 is CR 17 or N, and R 17 is hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6-C12) ) is an aryl group;
d는 0 또는 1 내지 3의 정수이며, e는 0 또는 1 내지 6의 정수이며, f 는 0 또는 1 내지 4의 정수로, g는 0 또는 1 내지 2의 정수이며, h는 0 또는 1 내지 7의 정수이며, d, e, f, g 및 h가 2이상의 정수인 경우 각 R21, R22 R24, R26 및 R27은 서로 동일하거나 상이할 수 있다.)d is 0 or an integer from 1 to 3, e is 0 or an integer from 1 to 6, f is 0 or an integer from 1 to 4, g is 0 or an integer from 1 to 2, h is 0 or an integer from 1 to 2 It is an integer of 7, and when d, e, f, g and h are integers of 2 or more, each of R 21 , R 22 R 24 , R 26 and R 27 may be the same or different from each other.)
분상성 및 저장안정성 측면에서 바람직하게 본 발명의 일 실시예에 따른 상기 화학식 1은 하기 화학식 2로 표시될 수 있다.In terms of dispersibility and storage stability, Formula 1 according to an embodiment of the present invention may be represented by Formula 2 below.
[화학식 2][Formula 2]
[상기 화학식 2에서,[In Formula 2 above,
X1 및 X2는 -NH-, -O-, -CONH-, -SO2-, -SO2NH-, -CH2NH-, -CH2- 또는 -CH2NHCOCH2NH-이며;X 1 and X 2 are -NH-, -O-, -CONH-, -SO 2 -, -SO 2 NH-, -CH 2 NH-, -CH 2 - or -CH 2 NHCOCH 2 NH-;
R1 은 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, -SO2N(R11)(R12) 또는 -CON(R13)(R14)이며, R11 내지 R14는 서로 독립적으로 수소, (C1-C5)알킬 또는 (C6-C12)아릴기이며;R 1 is a halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (C6-C12) Aryl group, -SO 2 N(R 11 )(R 12 ) or -CON(R 13 )(R 14 ), and R 11 to R 14 are independently hydrogen, (C1-C5)alkyl, or (C6-C12). ) is an aryl group;
a 는 서로 독립적으로 0 또는 1 내지 5의 정수이며, b는 1 내지 5의 정수로, a+b≤5이며, a 및 b가 2이상인 경우 R1은 서로 상이하거나 동일할 수 있으며;a is independently 0 or an integer from 1 to 5, b is an integer from 1 to 5, and a+b≤5, and when a and b are 2 or more, R 1 may be different from or the same as each other;
Ar1은 , 또는 이며;Ar 1 is , or and;
R21 내지 R22는 서로 독립적으로, 아미노기, 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, -SO2N(R11)(R12) 또는 -CON(R13)(R14) 이며, R11 내지 R14는 서로 독립적으로 수소, (C1-C5)알킬 또는 (C6-C12)아릴기이며;R 21 to R 22 are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) An alkoxycarbonyl group, (C6-C12)aryl group, -SO 2 N(R 11 )(R 12 ) or -CON(R 13 )(R 14 ), and R 11 to R 14 are independently hydrogen, (C1) -C5) alkyl or (C6-C12) aryl group;
D1은 CR15R16 또는 N이며, R15 및 R16은 서로 독립적으로 수소, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며; D 1 is CR 15 R 16 or N, and R 15 and R 16 are independently hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) It is an alkoxycarbonyl group or (C6-C12)aryl group;
d는 0 또는 1 내지 3의 정수이며, e는 0 또는 1 내지 6의 정수이며, h는 0 또는 1 내지 7의 정수이며, d, e 및 f가 2이상의 정수인 경우 각 R21, R22 및 R27은 서로 동일하거나 상이할 수 있다.)d is 0 or an integer of 1 to 3, e is 0 or an integer of 1 to 6, h is 0 or an integer of 1 to 7, and when d, e and f are integers of 2 or more, R 21 , R 22 and R 27 may be the same or different from each other.)
바람직하게 본 발명의 일 실시예에 따른 상기 화학식 2에서 X1 및 X2는 -NH-이며;Preferably, in Formula 2 according to an embodiment of the present invention, X 1 and X 2 are -NH-;
R1은 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;R 1 is a halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6-C12) It is an aryl group;
a는 0 또는 1 내지 5의 정수이며, b는 1 내지 5의 정수로, a+b≤5이며, a가 2이상인 경우 R1은 서로 상이하거나 동일할 수 있으며;a is 0 or an integer from 1 to 5, b is an integer from 1 to 5, and a+b≤5, and when a is 2 or more, R 1 may be different from or the same as each other;
Ar1은 , 또는 이며;Ar 1 is , or and;
R21 내지 R22 및 R27은 서로 독립적으로, 아미노기, 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며; R 21 to R 22 and R 27 are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1) -C5) alkoxycarbonyl group or (C6-C12) aryl group;
D1은 N이며; D 1 is N;
d는 0 또는 1 내지 3의 정수이며, e는 0 또는 1 내지 6의 정수이며, h는 0 또는 1 내지 7의 정수이며, d, e 및 h가 2이상의 정수인 경우 각 R21, R22 및 R27은 서로 동일하거나 상이할 수 있다. d is 0 or an integer of 1 to 3, e is 0 or an integer of 1 to 6, h is 0 or an integer of 1 to 7, and when d, e and h are integers of 2 or more, R 21 , R 22 and R 27 may be the same or different from each other.
구체적으로 본 발명의 일 실시예에 따른 상기 화학식 1의 트리아진 유도체는 하기 화합물에서 선택될 수 있으나, 이에 한정이 있는 것은 아니다.Specifically, the triazine derivative of Formula 1 according to an embodiment of the present invention may be selected from the following compounds, but is not limited thereto.
, ,
본 발명에 기재된 「알킬」, 「알콕시」 및 그 외 「알킬」부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함한다. Substituents containing “alkyl,” “alkoxy,” and other “alkyl” moieties described in the present invention include both straight-chain or branched forms.
본 발명에 기재된 「할로알킬」은 알킬기에 할로겐이 하나이상 치환된 형태를 의미하며, 일례로 트리플로오로메탄, 브로모메탄 등을 들 수 있다. “Haloalkyl” as used in the present invention refers to an alkyl group in which one or more halogens are substituted, and examples include trifluoromethane and bromomethane.
또한 본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐 등을 포함하지만, 이에 한정되지 않으며, 일례로 프탈이미드, 불포화된 인덴(2H-인덴-1,3-디온, 2,3-하이드로-1H-인덴), 이소인돌린, 안트라퀴논 등도 아릴기에 포함된다. In addition, “aryl” described in the present invention is an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen, and is a single or fused radical containing 4 to 7 ring atoms, preferably 5 or 6 ring atoms in each ring. It includes a ring system and even includes forms in which multiple aryls are connected by single bonds. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, etc., and examples include phthalimide, unsaturated indene (2H-indene-1,3- Dione, 2,3-hydro-1H-indene), isoindoline, anthraquinone, etc. are also included in the aryl group.
본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연결된 형태도 포함한다. “Heteroaryl” described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P(=O), Si and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. It refers to an aryl group, which is a 5- to 6-membered monocyclic heteroaryl and a polycyclic heteroaryl condensed with one or more benzene rings, and may be partially saturated. In addition, heteroaryl in the present invention also includes forms in which one or more heteroaryls are linked by a single bond.
본 발명에 기재된 트리아진 화합물은 본 발명의 기술분야에 해당되는 당업자가 인식할 수 있는 범위내에서 가능한 방법이라면 모두 가능하다.The triazine compound described in the present invention can be prepared by any method within the range recognized by a person skilled in the art.
먼저 염와 시아누르에 술폰산 화합물을 반응시켜 술폰산기를 도입한다.First, a sulfonic acid group is introduced by reacting the salt and cyanuric acid with a sulfonic acid compound.
일반적으로 염화 시아누르 1mol에 대한 술포산 화합물의 사용량은 보통 0.5 내지 1.5mol, 바람직하게는 0.9 내지 1.1mol일 수 있으며, 염화 시아누르와 술폰산 화합물의 반응은, 예를 들면 적절한 용매내에서 교반하거나 또는 교반하지 않고, -10 내지 0℃에서 1 내지 2시간 교반시킨 후 반응을 종료시킨다. 용매는 통상적으로 사용되는 용매라면 모두 가능하나, 예를 들면 물이나 아세톤, 다이옥산, 크실렌, 디메틸포름아미드, 테트라플루오르퓨란 등의 유기용매 혹은 2종 이상의 혼합 용매 등을 사용할 수 있다.In general, the amount of the sulfonate compound used per 1 mol of cyanuric chloride is usually 0.5 to 1.5 mol, preferably 0.9 to 1.1 mol, and the reaction between cyanuric chloride and the sulfonic acid compound can be carried out, for example, by stirring in an appropriate solvent. Alternatively, the reaction is terminated after stirring for 1 to 2 hours at -10 to 0°C without stirring. The solvent can be any commonly used solvent, but for example, organic solvents such as water, acetone, dioxane, xylene, dimethylformamide, tetrafluorofuran, or a mixed solvent of two or more types can be used.
다음으로 술폰산기가 도입된 반응물에 트리아진기를 가지는 치환기를 도입하기위해 일례로 아미노기를 하나이상 가지는 화합물을 적어도 1종을 반응시킨다. 이러한 화합물의 구체적인 예로서는, 4-아미노프탈이미드(4-amino phthalimide)등을 들 수 있다. 염화 시아누르와 술폰산 화합물과의 반응물 1mol에 대한 아미노기를 하나이상 가지는 화합물의 사용량은, 사용하는 화합물의 종류에 따라 적절하게 선택되지만, 보통은 0.5 내지 2.5mol, 바람직하게는 0.9 내지 2.0mol일 수 있다. 산성기가 도입된 트리아진 골격에 염기성기를 도입하는 반응에 있어서는, 아세트산, 안식향산, 구연산, 푸마르산, 글루콘산, 옥살산 등의 유기산이나, 염산, 황산, 질산 등의 무기산을 용매로 하여 사용해도 좋다. 이들의 산은, 바람직하게는 수용액의 형태로 사용한다.Next, in order to introduce a substituent having a triazine group into the reactant into which a sulfonic acid group has been introduced, at least one compound having one or more amino groups, for example, is reacted. Specific examples of such compounds include 4-amino phthalimide. The amount of the compound having at least one amino group used per 1 mol of the reaction product between cyanuric chloride and the sulfonic acid compound is appropriately selected depending on the type of compound used, but is usually 0.5 to 2.5 mol, preferably 0.9 to 2.0 mol. there is. In the reaction of introducing a basic group into the triazine skeleton into which an acidic group has been introduced, organic acids such as acetic acid, benzoic acid, citric acid, fumaric acid, gluconic acid, and oxalic acid, or inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid may be used as solvents. These acids are preferably used in the form of an aqueous solution.
마지막으로 트리아진 유도체 또는 피리미딘 유도체, 일례로 2-아미노-1,3,5-아미노트라아진(2-amino-1,3,5-triazine)를 도입하는 반응은, 적절한 용매중에서 교반하거나 또는 교반하지 않고, 30 내지 100℃에서 1 내지 10시간에서 반응을 종료시킨다. 용매로서는, 염화 시아누르와 술폰산 화합물과의 반응에서 사용되는 용매와 같은 것을 사용할 수 있다. 이에 따라 최종적으로 염기성기, 산성기 및 방향족기로 각각 상이한 치환기가 도입된 트리아진 유도체가 생성된다. 얻어진 트리아진 유도체는 예를 들면 여과, 수세, 건조라는 통상의 분리 정제 수단에 의하여 반응 혼합물 중에서 용이하게 정제할 수 있다. Lastly, the reaction of introducing a triazine derivative or pyrimidine derivative, such as 2-amino-1,3,5-aminotriazine, is stirred in an appropriate solvent or Without stirring, the reaction is terminated in 1 to 10 hours at 30 to 100°C. As the solvent, the same solvent used in the reaction between cyanuric chloride and a sulfonic acid compound can be used. Accordingly, a triazine derivative having different substituents introduced into a basic group, an acidic group, and an aromatic group is ultimately produced. The obtained triazine derivative can be easily purified from the reaction mixture by conventional separation and purification means, for example, filtration, washing with water, and drying.
바람직하게 본 발명의 트리아진 유도체는 산성기 및 안료와 친화력이 높은 트리아진 유도체 및 피리미딘 유도체인 작용기외에 나머지 하나의 작용기는 안료의 모체, 안료의 제조시의 출발물질 또는 중간체를 도입하는 것이 분산성을 향상시키기위한 측면에서 바람직하다. 일례로 본 발명의 트리아진 유도체는 산성기 및 트리아진 유도체 및 피리미딘 유도체인 작용기외에 나머지 하나의 작용기를 본 발명에 기재된 화합물1a 및 1b와 같이 프탈이미드 및 퀴놀린을 작용기로 도입하는 경우 프탈이미드 및 퀴놀린을 작용기로 가지는 프탈이미드계 안료 또는 퀴놀린계 안료, 일례로, Pigment Yellow 138의 안료 분산 조제 및 표면처리제로 사용되는 것이 바람직하며 본 발명에 기재된 화합물1c와 같이 안트라퀴논을 작용기로 도입하는 경우 안트라퀴논계 안료, 일례로 Pigment Red 177, 89, 83 및 Pigment Violet 5:1의 안료 분산 조제 및 표면처리제로 사용되는 것이 바람직하며, 로 표시되는 유도체를 작용기로 도입하는 경우는 Pigment Red 254, 255, 264, 270, 272 및 Pigment Orange 71, 73, 81의 안료 분산 조제 및 표면처리제로 사용되는 것이 보다 바람직하다.]Preferably, in the triazine derivative of the present invention, in addition to the acidic group and the functional group that is a triazine derivative and pyrimidine derivative with high affinity for the pigment, the remaining functional group is a pigment matrix, a starting material or an intermediate during the production of the pigment. It is desirable in terms of improving acidity. For example, in the triazine derivative of the present invention, in addition to the acidic group and the functional group that is the triazine derivative and pyrimidine derivative, the remaining functional group is introduced into the functional group such as phthalimide and quinoline as in compounds 1a and 1b described in the present invention. Phthalimide-based pigments or quinoline-based pigments having mead and quinoline as functional groups, for example, Pigment Yellow 138, are preferably used as pigment dispersion aids and surface treatment agents, and anthraquinone is introduced as a functional group like compound 1c described in the present invention. In this case, it is preferable to use anthraquinone pigments, such as Pigment Red 177, 89, 83 and Pigment Violet 5:1, as a pigment dispersion aid and surface treatment agent, When the derivative represented by is introduced as a functional group, it is more preferable to use it as a pigment dispersion aid and surface treatment agent for Pigment Red 254, 255, 264, 270, 272 and Pigment Orange 71, 73, and 81.]
또한 본 발명은 본 발명의 트리아진 유도체를 포함하는 안료 분산 조제를 제공한다.The present invention also provides a pigment dispersion aid containing the triazine derivative of the present invention.
본 발명의 안료 분산 조제는 본 발명의 트리아진 유도체를 사용함으로써 분산성이 높고 저장안정성이 높아 이를 포함하는 안료 분산액은 고농도에서도 우수한 분산성을 가지며, 이러한 안료 분산액을 포함하는 착색 감광성 수지 조성물을 이용하여 제조된 컬러필터등의 디스플레이는 고휘도 및 우수한 콘트라스 값을 가진다.The pigment dispersion aid of the present invention has high dispersibility and storage stability by using the triazine derivative of the present invention, so the pigment dispersion containing it has excellent dispersibility even at high concentrations, and a colored photosensitive resin composition containing such a pigment dispersion is used. Displays such as color filters manufactured using this method have high brightness and excellent contrast values.
또한 본 발명은 본 발명의 트리아진 유도체를 포함하는 안료 표면처리제를 제공한다.The present invention also provides a pigment surface treatment agent containing the triazine derivative of the present invention.
본 발명의 안료 표면처리제는 안료와 친화력이 높은 트리아진 유도체 또는 피리미딘 유도체를 치환기로 도입하여 안료의 다양한 기능기와 결합이 가능함으로써 안료 표면의 손상을 억제하고 조제안료간의 응집을 억제하는 현저한 효과를 가지는 본 발명의 트리아진 유도체를 포함함으로써 조제안료를 용이하게 안료화하여 미세안료를 제조할 수 있으며, 미세안료의 재응집을 억제한다. The pigment surface treatment agent of the present invention introduces a triazine derivative or pyrimidine derivative with high affinity to the pigment as a substituent and can combine with various functional groups of the pigment, thereby suppressing damage to the pigment surface and suppressing aggregation between the prepared pigments. By containing the triazine derivative of the present invention, the eggplant can easily convert the crude pigment into a pigment to produce fine pigments, and re-agglomeration of the fine pigments is suppressed.
또한 본 발명은 본 발명의 안료 분산 조제, 안료, 안료 분산제 및 용제를 포함하는 안료 분산액을 제공한다.The present invention also provides a pigment dispersion liquid containing the pigment dispersion aid, pigment, pigment dispersant, and solvent of the present invention.
본 발명의 안료 분산액에 사용되는 안료 분산 조제는 안료 100중량부에 대하여 1 내지 25중량부를 사용할 수 있으며, 바람직하게는 1 내지 10중량부로 사용될 수 있다.The pigment dispersion aid used in the pigment dispersion of the present invention can be used in an amount of 1 to 25 parts by weight, preferably 1 to 10 parts by weight, per 100 parts by weight of the pigment.
본 발명의 안료 분산액은 본 발명의 안료 분산 조제를 포함함으로써 분산성 및 저장안정성이 매우 우수하다.The pigment dispersion of the present invention has excellent dispersibility and storage stability by including the pigment dispersion aid of the present invention.
본 발명의 일 실시예에 따른 안료 분산액에 포함되는 안료는 유기안료라면 한정이 있는 것은 아니나, 아조계 안료 또는 축합계 안료일 수 있으며, 단독으로 사용하거나, 2종이상 조합하여 사용할 수 있다. The pigment contained in the pigment dispersion according to an embodiment of the present invention is not limited as long as it is an organic pigment, but may be an azo pigment or a condensation pigment, and may be used alone or in combination of two or more types.
구체적으로, 적색 안료로는 C.I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 49, 57, 60, 63, 64, 68, 69, 81, 83, 88, 101, 104, 108, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 272, 272, 273, 274, 275, 276 등을 들 수 있고, 이 중에서도 바람직하게는 C.I. Pigment Red ,122, 166, 168, 177, 179 202, 206, 207, 209, 224, 242, 254, 264, 269 등, 더욱 바람직하게는 C.I. Pigment Red 166, 177, 179, 209, 224, 254, 264, 269 등을 들 수 있다.Specifically, the red pigment is C.I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 49, 57, 60, 63, 64, 68, 69, 81, 83, 88, 101, 104, 108, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209 , 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255 , 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 272, 272, 273, 274, 275, 276, etc. Among these, preferred C.I. Pigment Red , 122, 166, 168, 177, 179 202, 206, 207, 209, 224, 242, 254, 264, 269, etc., more preferably C.I. Pigment Red 166, 177, 179, 209, 224, 254, 264, 269, etc. are included.
녹색 안료로는 C.I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55, 58, 59 등이 있고, 이중 바람직하게는 C.I. Pigment Green 7, 36, 58, 59 등을 들 수 있다. The green pigment is C.I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55, 58, 59, etc. Preferably C.I. Pigment Green 7, 36, 58, 59, etc. are included.
황색 안료로는 C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 198, 213 및 214 등을 들 수 있다. 이 중에서도 바람직하게는 C.I. Pigment Yellow 129, 138, 185 등을 들 수 있다. The yellow pigment is C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153 , 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188 , Examples include 193, 194, 199, 198, 213, and 214. Among these, preferably C.I. Pigment Yellow 129, 138, 185, etc. may be mentioned.
오렌지 안료로는 C.I. Pigment Orange 1, 2, 5, 13, 16, 17, 19, 20, 21, 22, 23, 24, 34, 36, 38, 39, 43, 46, 48, 49, 61, 62, 64, 65, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, 79 등을 들 수 있고, 바람직하게는 C.I. Pigment Orange 38, 71, 73 등을 들 수 있다. The orange pigment is C.I. Pigment Orange 1, 2, 5, 13, 16, 17, 19, 20, 21, 22, 23, 24, 34, 36, 38, 39, 43, 46, 48, 49, 61, 62, 64, 65, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, 79, etc., preferably C.I. Examples include Pigment Orange 38, 71, and 73.
본 발명의 일 실시예에 따른 안료는 부피평균입자지름이 10 내지 150nm일 수 있으며, 바람직하게는 30 내지 110nm이며 더 바람직하게는 40 내지 80nm일 수 있다.The pigment according to an embodiment of the present invention may have a volume average particle diameter of 10 to 150 nm, preferably 30 to 110 nm, and more preferably 40 to 80 nm.
또한 본 발명의 안료 분산액에 포함되는 안료는 본 발명의 트리아진 유도체를 포함하는 안료 표면처리제 존재하에 유기안료의 원료가 되는 화합물을 반응시키거나 조제안료를 안료화하여 얻을 수 있다.In addition, the pigment contained in the pigment dispersion of the present invention can be obtained by reacting a compound that is a raw material of an organic pigment in the presence of a pigment surface treatment agent containing the triazine derivative of the present invention or by turning a crude pigment into a pigment.
즉, 본 발명의 안료 분산액에 포함되는 안료는 조제안료를 본 발명의 트리아진 유도체로 표면처리아여 얻어진 미세안료일 수 있다.That is, the pigment contained in the pigment dispersion of the present invention may be a fine pigment obtained by surface treating a crude pigment with the triazine derivative of the present invention.
본 발명에서 조제안료라 함은 축합다환계 안료의 바탕이 되는 원료화합물을 반응시켜서 얻어지며 입자 지름이 큰(예를 들면 10∼수백 ㎛ 정도) 화합물로서, 그 자체로는 안료로서의 분산성이나 선명한 발색이 얻어지지 않는 것을 말한다. 이러한 축합다환계 안료의 조제안료는 공지의 방법으로 조제할 수 있다.In the present invention, the crude pigment is a compound obtained by reacting the raw material compounds that form the basis of the condensed polycyclic pigment and has a large particle diameter (for example, about 10 to several hundred ㎛), which itself has the dispersibility and vivid color as a pigment. This means that color development is not achieved. Preparation pigments of these condensed polycyclic pigments can be prepared by known methods.
본 발명에서는, 상기와 같은 조제안료를 상기 트리아진 유도체의 존재하에서 안료화할 수 있다. 본 발명에서 안료화한다는 것은, 조제안료의 입자 지름을 안료로서 적절한 입자 지름범위에 맞추는 공정을 의미한다. 또한 적절한 입자범위는 용도 등에 따라 상이하나, 0.05 내지 0.3㎛일 수 있다.In the present invention, the above-mentioned crude pigment can be pigmented in the presence of the triazine derivative. Pigmentation in the present invention means a process of adjusting the particle diameter of the prepared pigment to an appropriate particle diameter range as a pigment. Additionally, the appropriate particle range varies depending on the use, etc., but may be 0.05 to 0.3㎛.
또한 상기 안료화의 방법으로서는, 솔트 밀링 등의 공지의 방법을 사용하여 할 수 있다. 안료화할 시의 상기 트리아진 유도체의 첨가량은 특별하게 한정은 없으나, 조제안료 100중량부에 대하여 상기 트리아진 유도체가 0.1 내지 20중량부가 되도록 첨가할 수 있다. 상기 트리아진 유도체의 첨가량이 0.1중량부보다 적으면 결정성장 억제효과가 작고, 20중량부보다 많으면 최종제품의 투명성, 콘트라스트 등의 성능에 영향을 줄 수 있다.Additionally, as a method of pigmentation, a known method such as salt milling can be used. There is no particular limitation on the amount of the triazine derivative added during pigmentation, but the triazine derivative may be added in an amount of 0.1 to 20 parts by weight based on 100 parts by weight of the crude pigment. If the amount of the triazine derivative added is less than 0.1 parts by weight, the effect of inhibiting crystal growth is small, and if it is more than 20 parts by weight, it may affect performance such as transparency and contrast of the final product.
조제안료를 안료화한 후에 정법에 의하여 수세하여 건조시킨 후 롤밀, 비즈밀 등의 분산기로 분쇄함으로써, 고도로 미세화되어 1차입자 지름이 매우 작은 축합다환계 안료를 포함하는 미세안료 조성물을 얻을 수 있다.After converting the crude pigment into a pigment, washing it with water and drying it according to a conventional method, and pulverizing it with a disperser such as a roll mill or bead mill, a fine pigment composition containing highly refined condensed polycyclic pigments with a very small primary particle diameter can be obtained.
상기에서 언급한 바와 같이 하여 얻어진 본 발명의 트리아진 유도체와 원하는 유기안료를 포함하는 미세안료 조성물은, 원하는 유기안료가 고도로 미세화되어 있어, 예를 들면 유기안료의 1차 입자로서 장경이 50 내지 150nm, 단경이 30 내지 100nm를 구비하는 것을 얻을 수 있다. In the micropigment composition containing the triazine derivative of the present invention and the desired organic pigment obtained as mentioned above, the desired organic pigment is highly refined, for example, the primary particle of the organic pigment has a long diameter of 50 to 150 nm. , it can be obtained with a minor diameter of 30 to 100 nm.
또한 상기와 같이 제조된 미세안료 조성물은 유기안료의 1차 입자가 매우 작고 고도로 미세화되어 있는 동시에 응집성을 현저하게 억제할 수 있는 것으로, 안료 분산액에 분산시킨 경우에도 분산제 등과의 상승효과에 의하여 응집을 효과적으로 방지할 수 있어, 고휘도 및 우수한 콘트라스값을 갖는 컬러 필터용등의 착색 감광성 수지 조성물에 용이하게 적용할 수 있다.In addition, the micropigment composition prepared as described above has very small and highly refined primary particles of the organic pigment, and can significantly suppress agglomeration. Even when dispersed in a pigment dispersion, aggregation is prevented due to a synergistic effect with the dispersant. It can be effectively prevented and can be easily applied to colored photosensitive resin compositions for color filters with high brightness and excellent contrast values.
본 발명의 일 실시예에 따른 안료 분산제는 칼라필터용 착색 감광성 수지 조성물 제조에 통상적으로 사용되는 것으로, 예컨대, 아민기 또는 암모늄솔트기를 안료 친화기로서 포함하는 것이 적합하며, 이의 바람직한 예로는 아크릴계 공중합체, 폴리우레탄, 폴리에틸렌이민류 및 이들의 혼합물을 들 수 있다. 시판되는 분산제로는 BYK-케미(BYK-Chemie)사의 디스퍼빅(Disperbyk)-160, 디스퍼빅-161, 디스퍼빅-165, 디스퍼빅-168, 디스퍼빅-170, 디스퍼빅-171, 디스퍼빅-2000, 디스퍼빅-2001; 디스퍼빅-LN21116; 및 디스퍼빅-LPN6919, LPN-22102, LPN-22251, LPN-22238, LPN-22841, LPN-22421, LPN-22470, LPN-22558, LPN-22822, LPN-22964, LPN-22481, LPN-22484, LPN-22474, LPN-22480, LPN-22478, LPN-22475, LPN-23170, LPN-23171, LPN-23172; EFKA사의 EFKA-4046, EFKA-4047 및 EFKA-4340; 아베시아(AVECIA)사의 솔스퍼스(Solsperse)-5000, 솔스퍼스-12000, 솔스퍼스-22000, 솔스퍼스-24000, 및 솔스퍼스-32500; 및 아지노모토(AJINOMOTO) 사의 PB-821, PB-822, PB-824, PB-827 등이 있다. 이들 분산제는 각각 단독으로 또는 2종 이상 조합하여 사용할 수 있다. The pigment dispersant according to an embodiment of the present invention is commonly used in the production of colored photosensitive resin compositions for color filters, and for example, it is suitable to include an amine group or an ammonium salt group as a pigment affinity group, and a preferred example thereof is an acrylic-based dispersant. Examples include polymers, polyurethanes, polyethylene imines, and mixtures thereof. Commercially available dispersants include BYK-Chemie's Disperbyk-160, Disperbyk-161, Disperbyk-165, Disperbyk-168, Disperbyk-170, Disperbyk-171, and Disperbyk- 2000, Dispervik-2001; Disperbig-LN21116; and dispervic-LPN6919, LPN-22102, LPN-22251, LPN-22238, LPN-22841, LPN-22421, LPN-22470, LPN-22558, LPN-22822, LPN-22964, LPN-22481, LPN-22484, LPN-22474, LPN-22480, LPN-22478, LPN-22475, LPN-23170, LPN-23171, LPN-23172; EFKA-4046, EFKA-4047 and EFKA-4340 from EFKA; Solsperse-5000, Solsperse-12000, Solsperse-22000, Solsperse-24000, and Solsperse-32500 from AVECIA; and PB-821, PB-822, PB-824, and PB-827 from AJINOMOTO. These dispersants can be used individually or in combination of two or more types.
본 발명의 일 실시예에 따른 안료 분산제는 저장안정성과 안료 분산액을 포함하는 착색 감광성 수지 제조시 알칼리 현상액에 대한 현상속도가 느려져 현상 후 잔사가 남는 문제등의 측면에서 안료 분산제의 고형분을 기준으로 안료 100중량부에 대하여 10 내지 80중량부, 바람직하게는 10 내지 60 중량부, 더욱 바람직하게는 20 내지 50 중량부로 사용될 수 있다.The pigment dispersant according to an embodiment of the present invention is a pigment based on the solid content of the pigment dispersant in terms of storage stability and problems such as the problem of residue remaining after development due to slow development speed with alkaline developer when manufacturing colored photosensitive resin containing pigment dispersion. It can be used in an amount of 10 to 80 parts by weight, preferably 10 to 60 parts by weight, and more preferably 20 to 50 parts by weight, based on 100 parts by weight.
본 발명의 일 실시예에 따른 안료 분산액은 분산용 수지로 알칼리 가용성 수지를 더 포함할 수 있으며, 칼라필터용 착색 감광성 수지 조성물에 통상적으로 사용되는 것으로서, 선상의 고분자 중합체로서 유기 용매에 가용인 아크릴계 수지가 바람직하다. The pigment dispersion according to an embodiment of the present invention may further include an alkali-soluble resin as a dispersing resin, and is commonly used in colored photosensitive resin compositions for color filters, and is a linear polymer that is soluble in organic solvents. Resin is preferred.
상기 아크릴계 수지에 사용할 수 있는 단량체의 구체적인 예로서는, 분자 내에 1개 이상의 카복실기를 갖는 화합물(예컨대, 아크릴산, 메타크릴산, 말레산, 푸말산); 방향족 비닐 화합물 (예컨대, 스티렌, α-메틸스티렌, 비닐톨루엔, 비닐벤질메틸에테르, 벤질 (메타)아크릴레이트, 시클로헥실 (메타)아크릴레이트, 페닐 (메타)아크릴레이트 등); 불포화 카복실레이트 화합물 (예컨대, 메틸 (메타)아크릴레이트, 에틸 (메타)아크릴레이트, 부틸 (메타)아크릴레이트); 수산기를 갖는 화합물(예컨대, 2-하이드록시알킬(메타)아크릴레이트, 글리세롤(메타)아크릴레이트); 친수성을 갖는 화합물(예컨대, (메타)아크릴아미드, 2차 또는 3차 아킬아크릴아미드, 디알킬아미노알킬(메타)아크릴레이트, N-비닐피롤리돈, N-비닐카프로락탐, 비닐이미다졸, 비닐트리아졸); 분기 또는 직쇄의 부틸(메타)아크릴레이트, 에틸헥실(메타)아크릴레이트, 페녹시하이드록시프로필(메타)아클릴레이트; 기타, 상기 친수성을 갖는 화합물로서, 테트라하이드로푸르푸릴기, 인산부위, 인산에스테르부위, 4차 암모늄염의 부위, 에틸렌옥시쇄, 프로필렌옥시쇄, 술폰산기 등을 함유하는 단량체 등을 들 수 있다. Specific examples of monomers that can be used in the acrylic resin include compounds having one or more carboxyl groups in the molecule (eg, acrylic acid, methacrylic acid, maleic acid, fumaric acid); aromatic vinyl compounds (e.g., styrene, α-methylstyrene, vinyltoluene, vinylbenzylmethyl ether, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, phenyl (meth)acrylate, etc.); unsaturated carboxylate compounds (e.g., methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate); Compounds having a hydroxyl group (e.g., 2-hydroxyalkyl (meth)acrylate, glycerol (meth)acrylate); Compounds having hydrophilic properties (e.g., (meth)acrylamide, secondary or tertiary akylacrylamide, dialkylaminoalkyl (meth)acrylate, N-vinylpyrrolidone, N-vinylcaprolactam, vinylimidazole, vinyltriazole); Branched or straight-chain butyl (meth)acrylate, ethylhexyl (meth)acrylate, phenoxyhydroxypropyl (meth)acrylate; Other examples of the hydrophilic compound include monomers containing a tetrahydrofurfuryl group, a phosphoric acid moiety, a phosphate ester moiety, a quaternary ammonium salt moiety, an ethylene oxy chain, a propylene oxy chain, and a sulfonic acid group.
가교 효율성을 높이기 위해, 수지가 측쇄에 중합성기를 가질 수 있다. To increase crosslinking efficiency, the resin may have a polymerizable group on the side chain.
상기 아크릴계 수지는 중량평균분자량(GPC법 측정, 폴리스티렌 환산값)이 1,000 내지 200,000인 것이 바람직하며, 더욱 바람직하게는 2,000 내지 50,000이다.The acrylic resin preferably has a weight average molecular weight (measured by GPC method, converted to polystyrene) of 1,000 to 200,000, more preferably 2,000 to 50,000.
분산성 수지는 본 발명의 안료 100중량부를 기준으로 10 내지 80 중량부 바람직하게는 10 내지 60 중량부, 더욱 바람직하게는 20 내지 50중량부로 사용될 수 있다.The dispersible resin may be used in an amount of 10 to 80 parts by weight, preferably 10 to 60 parts by weight, and more preferably 20 to 50 parts by weight, based on 100 parts by weight of the pigment of the present invention.
본 발명의 일 실시예에 따른 안료 분산액에 사용되는 용매는 통상적으로 알려진 각종 용매를 특별한 제한 없이 사용할 수 있다. 구체적인 예로는 에틸렌글리콜모노메틸에테르, 에틸렌글리콜모노에틸에테르, 프로필렌글리콜모노메틸에테르, 프로필렌글리콜모노에틸에테르, 디에틸렌글리콜모노메틸에테르, 디에틸렌글리콜모노에틸에테르 등의 알킬렌글리콜모노알킬에테르 및 이들의 초산에스테르류, 메틸에틸케톤, 아세톤, 메틸이소부틸케톤, 시클로헥사논 등의 케톤류, 감마-부티로락톤, 에틸락테이트, 부틸락테이트 및 에틸피루베이트를 들 수 있다. 이들 용매는 각각 단독으로 또는 2종 이상 조합하여 사용할 수 있다. As the solvent used in the pigment dispersion according to an embodiment of the present invention, various commonly known solvents can be used without particular limitation. Specific examples include alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and these. acetic acid esters, ketones such as methyl ethyl ketone, acetone, methyl isobutyl ketone, and cyclohexanone, gamma-butyrolactone, ethyl lactate, butyl lactate, and ethyl pyruvate. These solvents can be used individually or in combination of two or more.
용매는 안료 분산액 총 중량을 기준으로 바람직하게는 70 내지 90중량%, 더욱 바람직하게는 75 내지 85중량%의 양으로 사용할 수 있다. The solvent may be used in an amount of preferably 70 to 90% by weight, more preferably 75 to 85% by weight, based on the total weight of the pigment dispersion.
본 발명의 일실시예에 따른 안료 분산액은 안료의 분산 안정성 향상, 열 안정성 및 알칼리 현상성등을 향상시키기위해 통상적인 계면활성제 또는 유기산 등을 첨가제로 더 포함할 수 있다.The pigment dispersion according to an embodiment of the present invention may further include a conventional surfactant or organic acid as an additive to improve the dispersion stability, heat stability, and alkali developability of the pigment.
본 발명의 일 실시예에 따른 안료 분산액에 사용되는 계면활성제로는 통상적으로 알려진 각종 계면활성제를 특별한 제한 없이 사용할 수 있으며, 시판되는 계면활성제로는 메가팍(Megafac) R08 및 메가팍 F477 (다이니폰 잉크 앤 케미컬즈사 제조) 등이 있다.As the surfactant used in the pigment dispersion according to an embodiment of the present invention, various commonly known surfactants can be used without particular limitation, and commercially available surfactants include Megafac R08 and Megafac F477 (Dainipon (manufactured by Ink & Chemicals), etc.
본 발명의 안료 분산액은 본 발명의 트리아진 유도체를 포함함으로써 저장안정성 및 분산성이 높아 이를 채용한 착색 감광성 수지 조성물을 이용한 컬러필터등의 디스플레이의 휘도 및 명암비 특성을 현저하게 향상시킨다.The pigment dispersion of the present invention has high storage stability and dispersibility by containing the triazine derivative of the present invention, thereby significantly improving the brightness and contrast ratio characteristics of displays such as color filters using colored photosensitive resin compositions employing the triazine derivative of the present invention.
또한 본 발명은 본 발명의 안료 분산액 및 감광성 화합물을 포함하는 착색 감광성 수지 조성물을 제공한다.The present invention also provides a colored photosensitive resin composition comprising the pigment dispersion of the present invention and a photosensitive compound.
본 발명의 감광성 화합물을 통상적으로 착색제일 수 있으며, 착색제는 안료, 염료 또는 이들의 혼합물일 수 있다.The photosensitive compound of the present invention may typically be a colorant, and the colorant may be a pigment, dye, or a mixture thereof.
안료는 상기에 기재된 안료가 사용될 수 있으며, 염료로는 통상적으로 착색제로 사용되는 염료는 모두 가능하며, 이러한 구체적인 예로는 액시드 옐로우(acid yellow) 1, 3, 5, 7, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 134, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; 솔벤트 옐로우(solvent yellow) 14, 23, 38, 62, 63, 64, 68, 78, 82, 89, 90, 91, 92, 94, 98, 99, 104, 105, 106, 126, 128, 129, 130, 132, 133, 134, 138, 139, 140, 144, 145, 156, 160, 161, 162, 163, 164, 165, 168, 169, 170, 171; 액시드 레드(acid red) 29, 31, 51, 52, 92, 94, 97, 133, 134, 158, 176, 183, 198, 249, 266, 289, 308; 액시드 오렌지(acid orange)6, 7, 8, 10, 12, 26, 51, 52, 62, 63, 64, 74, 107, 169 등이 있다. The pigments described above can be used, and the dyes can be any dyes commonly used as colorants. Specific examples include acid yellow 1, 3, 5, 7, 11, 17, 23. , 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 134 , 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 2 04 , 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; Solvent yellow 14, 23, 38, 62, 63, 64, 68, 78, 82, 89, 90, 91, 92, 94, 98, 99, 104, 105, 106, 126, 128, 129, 130, 132, 133, 134, 138, 139, 140, 144, 145, 156, 160, 161, 162, 163, 164, 165, 168, 169, 170, 171; acid red 29, 31, 51, 52, 92, 94, 97, 133, 134, 158, 176, 183, 198, 249, 266, 289, 308; There are acid oranges 6, 7, 8, 10, 12, 26, 51, 52, 62, 63, 64, 74, 107, 169, etc.
본 발명의 일 실시예에 따른 착색 감광성 수지 조성물은 광개시제 및 가교제를 더 포함할 수 있으며, 본 발명에 사용되는 광개시제로는 통상적으로 알려진 각종 광개시제 화합물을 특별한 제한 없이 사용할 수 있다. 이의 구체적인 예로는 요오드염 화합물, 술포늄염 화합물, 유기할로겐 화합물, 옥심 화합물 및 이들의 혼합물을 들 수 있다. 시판되는 광개시제로는 시바 가이기(Ciba Geigy)사의 이르가큐어(Irgacure)-907, 이르가큐어-369, 이르가큐어 OXE 01, 이르가큐어 OXE 02 등이 있다. 광개시제는 착색 감광성 수지 조성물 총 중량을 기준으로 바람직하게는 0.1 내지 5 중량%의 양으로 사용할 수 있다. 각 광개시제는 1종을 단독으로 사용하거나 또는 2종 이상을 조합하여 사용할 수 있다. 본 발명에 사용되는 가교제는 통상적으로 알려진 각종 가교제 화합물을 특별한 제한 없이 사용할 수 있다. 구체적인 예로는, 에틸렌글리콜 디(메타)아크릴레이트, 에틸렌기의 수가 2 내지 14개인 폴리에틸렌글리콜 디(메타)아크릴레이트, 트리메틸올프로판 디(메타)아크릴레이트, 트리메틸올프로판 트리(메타)아크릴레이트, 펜타에리스리톨 트리(메타)아크릴레이트, 펜타에리스리톨 테트라(메타)아크릴레이트, 2-트리스아크릴로일옥시메틸에틸프탈산, 프로필렌글리콜 디(메타)아크릴레이트, 프로필렌기의 수가 2 내지 14개인 폴리프로필렌글리콜 디(메타)아크릴레이트, 디펜타에리스리톨 펜타(메타)아크릴레이트 및 디펜타에리스리톨 헥사(메타)아크릴레이트 등을 들 수 있다. 이들 가교제는 각각 단독으로 또는 2종 이상 조합하여 사용할 수 있다. 가교제는 착색 감광성 수지 조성물 총 중량을 기준으로 바람직하게는 0.5 내지 10 중량%의 양으로 사용할 수 있다. The colored photosensitive resin composition according to an embodiment of the present invention may further include a photoinitiator and a crosslinking agent, and as the photoinitiator used in the present invention, various commonly known photoinitiator compounds may be used without particular limitation. Specific examples thereof include iodine salt compounds, sulfonium salt compounds, organic halogen compounds, oxime compounds, and mixtures thereof. Commercially available photoinitiators include Irgacure-907, Irgacure-369, Irgacure OXE 01, and Irgacure OXE 02 from Ciba Geigy. The photoinitiator may be preferably used in an amount of 0.1 to 5% by weight based on the total weight of the colored photosensitive resin composition. Each photoinitiator can be used individually or in combination of two or more types. The cross-linking agent used in the present invention can be any of various commonly known cross-linking agent compounds without any particular restrictions. Specific examples include ethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate having 2 to 14 ethylene groups, trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, Pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 2-trisacryloyloxymethylethylphthalic acid, propylene glycol di(meth)acrylate, polypropylene glycol di having 2 to 14 propylene groups. (meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate. These crosslinking agents can be used individually or in combination of two or more. The crosslinking agent may be preferably used in an amount of 0.5 to 10% by weight based on the total weight of the colored photosensitive resin composition.
본 발명의 트리아진 유도체를 포함하는 안료 분산액을 채용한 착색 감광성 수지 조성물은 우수한 투명성과 착색력을 가지므로 저전력의 고색재현용 칼라필터의 제조에 매우 유용하게 사용될 수 있다.The colored photosensitive resin composition employing the pigment dispersion containing the triazine derivative of the present invention has excellent transparency and coloring power and can be very useful in the production of a low-power, high-color reproduction color filter.
이하 본 발명을 실시예에 의해 상세하게 설명한다. 그러나 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 내용이 하기 실시예에 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail by examples. However, the following examples are merely illustrative of the present invention and the content of the present invention is not limited to the following examples.
[실시예 1] 화합물1a의 제조[Example 1] Preparation of Compound 1a
염화 시아누르 ( 9.3)g을 아세톤 (500 )mL녹이고 여기에 염화 시아누르 1개의 염소원자와 반응하는 양의 설파닐산(Sulfanilic acid) (8.6)g을 가하여 0℃에서 1시간 반응시켰다. 여기서 4-아미노프탈이미드 (4-amino phthalimide) 8.1g을 첨가하고 40℃에서 1시간 반응시켰다. 이어서 2-아미노트리아진(2-amino-1,3,5-triazine)을 추가적으로 (8.1)g을 첨가하고 90℃에서 5시간 반응시켰다. 얻어진 반응물을 침출시켜 생성된 잔사를 수세한 후, 100℃의 항온조에 밤새 정치해서 건조시켜서, 목적물인 화합물 1a(18.9)g을 얻었다. (LC/MS, m/z= 506)Cyanuric chloride (9.3) g was dissolved in acetone (500 mL), and sulfanilic acid (8.6) g, an amount that reacts with one chlorine atom of cyanuric chloride, was added and reacted at 0°C for 1 hour. Here, 8.1 g of 4-amino phthalimide was added and reacted at 40°C for 1 hour. Subsequently, (8.1) g of 2-amino-1,3,5-triazine was added and reacted at 90°C for 5 hours. The obtained reaction product was leached and the resulting residue was washed with water, left in a thermostat at 100°C overnight, and dried to obtain the target compound 1a (18.9) g. (LC/MS, m/z=506)
[실시예 2] 화합물1b의 제조[Example 2] Preparation of compound 1b
실시예 1에서 4-아미노프탈이미드 대신 8-아미노퀴놀린(8-amino quinoline, 7.2g)을 첨가한 것을 제외하고는 실시예 1과 동일하게 제조하여 화합물 1b, (18.2)g을 얻었다. (LC/MS, m/z=488)Compound 1b, (18.2) g was obtained in the same manner as in Example 1, except that 8-amino quinoline (7.2 g) was added instead of 4-aminophthalimide. (LC/MS, m/z=488)
[실시예 3] 화합물1c의 제조[Example 3] Preparation of compound 1c
실시예 1에서 4-아미노프탈이미드 대신 2-아미노안트라퀴논 (2-aminoanthraquinone, 11.2g)을 첨가한 것을 제외하고는 실시예 1과 동일하게 제조하여 화합물 1c, (19.3)g을 얻었다. (LC/MS, m/z=567)Compound 1c, (19.3) g was obtained in the same manner as in Example 1, except that 2-aminoanthraquinone (11.2 g) was added instead of 4-aminophthalimide. (LC/MS, m/z=567)
[실시예 4 내지 실시예 5] 안료 분산액의 제조[Examples 4 to 5] Preparation of pigment dispersion
하기 표 1에 나타낸 성분 및 사용량을 내용량 1000mL의 혼합기에 투입하고 지름 1.0mm 지르코니아 비즈(zirconia beads) 360g을 넣고, 디스퍼(disper)로 200rpm에서 60분간 교반하여 예비 분산을 하여 예비 분산물을 제조하였다.The ingredients and usage amounts shown in Table 1 below were put into a mixer with an net capacity of 1000 mL, 360 g of zirconia beads with a diameter of 1.0 mm were added, and stirred with a disper at 200 rpm for 60 minutes to prepare a preliminary dispersion. did.
상기에서 예비 분산물을 325 SUS MESH로 걸러 얻어진 200g에 지름 0.1mm의 지르코니아 비즈(zirconia beads) 400g을 200rpm으로 10시간 교반하여, 본분산하여 본 분산물을 얻었다. 얻어진 본 분산물에 PGMEA 100g을 첨가하고, 다시 200rpm으로 10분 교반하였다. 얻어진 최종 분산물을 0.45μm PP 필터 (Whatman 0.45 PP Filter, Whatman 제품)로 여과하여, 황색 안료 분산액을 얻었다.400 g of zirconia beads with a diameter of 0.1 mm were stirred at 200 rpm for 10 hours to 200 g of the preliminary dispersion obtained by filtering it through 325 SUS MESH, and the main dispersion was obtained. 100 g of PGMEA was added to the obtained dispersion, and stirred again at 200 rpm for 10 minutes. The obtained final dispersion was filtered through a 0.45 μm PP filter (Whatman 0.45 PP Filter, Whatman product) to obtain a yellow pigment dispersion.
마찬가지로 트리아진 화합물 1a 대신 본 발명의 실시예 2에서 제조한 트리아진 화합물 1b를 사용한 것을 제외하고는 상기와 동일하게 실시하여 안료 분산액을 각각 제조하였다.Likewise, pigment dispersions were prepared in the same manner as above, except that triazine compound 1b prepared in Example 2 of the present invention was used instead of triazine compound 1a.
[실시예 6] 안료 분산액의 제조[Example 6] Preparation of pigment dispersion
실시예 4에서 C.I. Pigment Yellow 138 대신 C.I. Pigment Red 177를 사용하고 트리아진 화합물 1a 대신 1c를 사용한 것을 제외하고는 실시예 4와 동일하게 실시하여 안료 분산액을 제조하였다.In Example 4, C.I. Pigment Yellow 138 instead of C.I. A pigment dispersion was prepared in the same manner as in Example 4, except that Pigment Red 177 was used and 1c was used instead of triazine compound 1a.
[비교예 1 내지 2]비교안료 분산액의 제조 [Comparative Examples 1 to 2] Preparation of comparative pigment dispersion
실시예 4에서 본 발명의 실시예 1에서 제조된 트리아진 화합물 대신 하기의 비교화합물 1 또는 하기의 비교화합물 2를 사용하여 안료 분산액을 제조한 것을 제외하고는 실시예 4와 동일하게 실시하여 안료 분산액을 제조하였다.A pigment dispersion was prepared in the same manner as in Example 4, except that the pigment dispersion was prepared using Comparative Compound 1 below or Comparative Compound 2 below instead of the triazine compound prepared in Example 1 of the present invention. was manufactured.
비교화합물 1은 하기와 같이 제조하였다.Comparative compound 1 was prepared as follows.
500mL 4구 플라스크에 25% 발연 황산과 황산으로부터 조제한 101% 황산 450g을 투입하고, C.I. 안료 옐로우 138, 45g을 조금씩 첨가했다. 80℃에서 3시간 동안 교반을 시키고, 반응 용액을 얼음물 5000부 중에 교반하면서 술폰화물을 석출시켰다. 석출한 술폰화물을 여과 분리하고, 0.1% 염산 2L로 세정하고, 정제수 2L로 더 세정하여 안료의 술폰화물(43g)을 얻었다.450 g of 101% sulfuric acid prepared from 25% fuming sulfuric acid and sulfuric acid was added to a 500 mL four-necked flask, and C.I. Pigment Yellow 138, 45g, was added little by little. The mixture was stirred at 80°C for 3 hours, and the sulfonate was precipitated while the reaction solution was stirred in 5000 parts of ice water. The precipitated sulfonated product was separated by filtration, washed with 2 L of 0.1% hydrochloric acid, and further washed with 2 L of purified water to obtain the sulfonated product of the pigment (43 g).
원소분석(C27H7Cl8NO7S) 계산치: C 41.95; H 0.91; Cl 36.69; N 1.81; O 14.49; S 4.15; 측정치: C 41.90; H 0.96; Cl 36.63; N 1.74; O 14.40; S 4.06Elemental analysis (C27H7Cl8NO7S) calculated: C 41.95; H 0.91; Cl 36.69; N 1.81; O 14.49; S 4.15; Measurements: C 41.90; H 0.96; Cl 36.63; N 1.74; O 14.40; S 4.06
하기의 비교화합물 2는 한국공개특허공보 제2011-0013320에 기재된 바와 동일하게 하기와 같이 제조하였다.Comparative Compound 2 below was prepared in the same manner as described in Korean Patent Publication No. 2011-0013320.
염화 시아누르 (9.3)g을 아세톤 500mL녹이고 여기에 염화 시아누르 1개의 염소원자와 반응하는 양의 설파닐산(Sulfanilic acid) (8.6g)을 가하여 0℃에서 1시간 반응시켰다. 여기서 4,4’-메틸렌비스(2,6-다이메틸아닐린) (4,4’-methylenebis(2,6-dimethylaniline)(15.8g)을 첨가하고 40℃에서 1시간 반응시켰다. 얻어진 반응물을 침출시켜 생성된 잔사를 수세한 후, 100℃의 항온조에 밤새 정치해서 건조시켜서, 목적물인 트리아진 화합물 1 (23.5)g을 얻었다.Cyanuric chloride (9.3) g was dissolved in 500 mL of acetone, and sulfanilic acid (8.6 g) in an amount that reacts with one chlorine atom of cyanuric chloride was added and reacted at 0°C for 1 hour. Here, 4,4'-methylenebis(2,6-dimethylaniline) (15.8 g) was added and reacted at 40°C for 1 hour. The obtained reactant was leached. The resulting residue was washed with water, left in a thermostat at 100°C overnight, and dried to obtain the target product, triazine compound 1 (23.5) g.
[비교예 3 내지 4]비교안료 분산액의 제조 [Comparative Examples 3 to 4] Preparation of comparative pigment dispersion
비교예 1 내지 2에서 C.I. Pigment Green 58 대신 C.I. Pigment Red 254를 사용한 것을 제외하고는 비교예 1 내지 2과 동일하게 제조하여 적색안료 분산액을 제조하였다.In Comparative Examples 1 to 2, C.I. Pigment Green 58 instead of C.I. A red pigment dispersion was prepared in the same manner as Comparative Examples 1 and 2, except that Pigment Red 254 was used.
[실시예 7 내지 8]착색 감광성 수지 조성물의 제조[Examples 7 to 8] Preparation of colored photosensitive resin composition
녹색안료 분산액의 제조Preparation of green pigment dispersion
하기 표 2에 나타낸 성분 및 함량을 내용량 1000mL의 혼합기에 투입하고 지름 1.0mm 지르코니아 비즈(zirconia beads) 360g을 넣고, 디스퍼(disper)로 200rpm에서 60분간 교반하여 예비 분산을 하여 예비 분산물을 제조하였다.The ingredients and contents shown in Table 2 below were put into a mixer with an net capacity of 1000 mL, 360 g of zirconia beads with a diameter of 1.0 mm were added, and stirred with a disper at 200 rpm for 60 minutes to prepare a preliminary dispersion. did.
상기의 예비 분산물을 325 SUS MESH로 걸러 얻어진 200g에 지름 0.1mm의 지르코니아 비즈(zirconia beads) 400g을 200rpm으로 10시간 교반하여, 본분산하여 본 분산물을 얻었다. 얻어진 본 분산물에 PGMEA 100g을 첨가하고, 다시 200rpm으로 10분 교반하였다. 얻어진 최종 분산물을 0.45μm PP 필터 (Whatman 0.45 PP Filter, Whatman 제품)로 여과하여, 녹색 안료 분산액을 얻었다.The preliminary dispersion was filtered through 325 SUS MESH, and 400 g of zirconia beads with a diameter of 0.1 mm were stirred for 10 hours at 200 rpm for 200 g to obtain the main dispersion. 100 g of PGMEA was added to the obtained dispersion, and stirred again at 200 rpm for 10 minutes. The obtained final dispersion was filtered through a 0.45 μm PP filter (Whatman 0.45 PP Filter, Whatman product) to obtain a green pigment dispersion.
실시예 4에서 각각 얻어진 황색 안료 분산액을 상기에서 얻어진 녹색 안료 분산액 과 4:6(중량비)으로 혼합하여 각각의 착색 감광성 수지 조성물을 제조하였으며, 얻어진 착색 감광성 수지 조성물을 스핀코터를 이용하여 각각의 필름을 형성한 후 100℃의 hot-plate에서 10분간 건조하여 코팅 필름을 얻었다. 얻은 코팅 필름을 초고압 수은등을 사용하여 100mJ/cm2의 광량으로 노광하고 알칼리 현상액으로 현상한 후 초순수로 세정하였다. 현상한 코팅 필름을 230℃의 오븐에서 20분간 열경화(post-bake)하여 칼라 필터용 패턴을 형성하였다. 열경화된 코팅 필름의 색도(x,y,Y)를 색도계 MCPD-3000(오츠카사 제조)을 사용하여 측정하였으며, 그 결과를 하기 표 3에 나타내었다.Each colored photosensitive resin composition was prepared by mixing the yellow pigment dispersion obtained in Example 4 with the green pigment dispersion obtained above at a ratio of 4:6 (weight ratio), and the obtained colored photosensitive resin composition was coated on each film using a spin coater. After forming, it was dried on a hot-plate at 100°C for 10 minutes to obtain a coating film. The obtained coating film was exposed to light of 100 mJ/cm 2 using an ultra-high pressure mercury lamp, developed with an alkaline developer, and then washed with ultrapure water. The developed coating film was heat-cured (post-bake) in an oven at 230°C for 20 minutes to form a pattern for a color filter. The chromaticity (x, y, Y) of the heat-cured coating film was measured using a colorimeter MCPD-3000 (manufactured by Otsuka Corporation), and the results are shown in Table 3 below.
[비교예 5 및 6] 착색 감광성 수지 조성물의 제조[Comparative Examples 5 and 6] Preparation of colored photosensitive resin composition
실시예 7 내지 8에서 실시예 4 및 실시예 5 대신 비교예 1 및 2의 안료 분산액을 사용한 것을 제외하고는 실시예 7 내지 8과 동일하게 착색 감광성 수지 조성물을 제조하였으며, 실시예 7 내지 8과 동일하게 칼라 필터용 패턴을 형성하였다. 열경화된 코팅 필름의 색도(x,y,Y)를 색도계 MCPD-3000(오츠카사 제조)을 사용하여 측정하였으며, 그 결과를 하기 표 3에 나타내었다.Colored photosensitive resin compositions were prepared in the same manner as in Examples 7 to 8, except that the pigment dispersions of Comparative Examples 1 and 2 were used instead of Examples 4 and 5 in Examples 7 to 8. In the same way, a pattern for a color filter was formed. The chromaticity (x, y, Y) of the heat-cured coating film was measured using a colorimeter MCPD-3000 (manufactured by Otsuka Corporation), and the results are shown in Table 3 below.
(Lv. 1~5)Sublimable substances
(Lv. 1~5)
[실시예 9 내지 비교예 7 내지 8]착색 감광성 수지 조성물의 제조[Example 9 to Comparative Examples 7 to 8] Preparation of colored photosensitive resin composition
적색안료 분산액의 제조Preparation of red pigment dispersion
실시예 7 내지 8에서 C.I. Pigment Green 58 대신 C.I. Pigment Red 254를 사용한 것을 제외하고는 실시예 7 내지 8과 동일하게 제조하여 적색안료 분산액을 제조하였다.In Examples 7 to 8, C.I. Pigment Green 58 instead of C.I. A red pigment dispersion was prepared in the same manner as in Examples 7 and 8, except that Pigment Red 254 was used.
또한 실시예 7 내지 8에서 실시예 4 내지 5에서 제조된 안료 분산액 대신 실시예 6에서 제조된 안료 분산액을 사용하고 상기에서 제조된 적색안료 분산액을 사용한 것을 제외하고는 실시예 7 내지 8과 동일하게 실시하여 착색 감광성 수지 조성물을 제조하였으며, 실시예 7 내지 8과 동일하게 칼라 필터용 패턴을 형성하였다. 열경화된 코팅 필름의 색도(x,y,Y)를 색도계 MCPD-3000(오츠카사 제조)을 사용하여 측정하였으며, 그 결과를 하기 표 4에 나타내었다.In addition, in Examples 7 to 8, the pigment dispersion prepared in Example 6 was used instead of the pigment dispersion prepared in Examples 4 to 5, and the red pigment dispersion prepared above was used in the same manner as Examples 7 to 8. A colored photosensitive resin composition was prepared, and a pattern for a color filter was formed in the same manner as Examples 7 and 8. The chromaticity (x, y, Y) of the heat-cured coating film was measured using a colorimeter MCPD-3000 (manufactured by Otsuka Corporation), and the results are shown in Table 4 below.
[비교예 7 내지 8]착색 감광성 수지 조성물의 제조[Comparative Examples 7 to 8] Preparation of colored photosensitive resin composition
실시예 9에서 실시예 6에서 제조된 안료 분산액 대신 비교예 3 내지 4에서 제조된 안료 분산액을 사용하고 실시예 9에서 제조된 적색안료 분산액을 사용한 것을 제외하고는 실시예 9와 동일하게 실시하여 착색 감광성 수지 조성물을 제조하였다.Coloring was carried out in the same manner as in Example 9, except that in Example 9, the pigment dispersion prepared in Comparative Examples 3 to 4 was used instead of the pigment dispersion prepared in Example 6, and the red pigment dispersion prepared in Example 9 was used. A photosensitive resin composition was prepared.
실시예 9와 동일하게 칼라 필터용 패턴을 형성하여 열경화된 코팅 필름의 색도(x,y,Y)를 색도계 MCPD-3000(오츠카사 제조)을 사용하여 측정하였으며, 그 결과를 하기 표 4에 나타내었다.In the same manner as in Example 9, the color filter pattern was formed and the chromaticity (x, y, Y) of the heat-cured coating film was measured using a colorimeter MCPD-3000 (manufactured by Otsuka Corporation), and the results are shown in Table 4 below. indicated.
(Lv. 1~5)Sublimable substances
(Lv. 1~5)
상기 표 3 및 표 4에서 보이는 바와 같이 본 발명의 트리아진 유도체를 포함하는 안료 분산액을 사용한 착색 감광성 수지 조성물이 비교예의 화합물을 포함한 안료 분산액을 사용한 착색 감광성 수지 조성물과 대비하여 우수한 Y값(투과율)을 나타내며, 또한 우수한 상대 휘도값을 가짐을 확인할 수 있었다.As shown in Tables 3 and 4, the colored photosensitive resin composition using the pigment dispersion containing the triazine derivative of the present invention has an excellent Y value (transmittance) compared to the colored photosensitive resin composition using the pigment dispersion containing the compound of the comparative example. It was also confirmed that it had an excellent relative luminance value.
Claims (11)
[화학식 1]
(상기 화학식 1에서,
X1 및 X2는 -NH-이며;
Ar1은 (C6-C12)아릴기 또는 (C3-C12)헤테로아릴기이며;
R1 및 R2는 서로 독립적으로 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, -SO2N(R11)(R12) 또는 -CON(R13)(R14)이며, R11 내지 R14는 서로 독립적으로 수소, (C1-C5)알킬 또는 (C6-C12)아릴기이며;
Z는 CR3 또는 N이며, R3은 수소, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;
a는 0 또는1 내지 5의 정수이며, b는 1 내지 5의 정수로, a+b≤5이며, a및 b가 2이상인 경우 R1은 서로 상이하거나 동일할 수 있으며;
c는 0 또는 1 내지 2의 정수로 c가 2이상인 경우 R2는 서로 상이하거나 동일할 수 있으며;
상기 Ar1의 아릴기 또는 헤테로아릴기는 아미노기, 카르복실산기, (C6-C12)아릴기, 및 -CON(R13)(R14)에서 선택되는 어느 하나이상으로 치환될 수 있다.)A triazine derivative represented by the following formula (1).
[Formula 1]
(In Formula 1 above,
X 1 and X 2 are -NH-;
Ar 1 is a (C6-C12)aryl group or (C3-C12)heteroaryl group;
R 1 and R 2 are independently of each other halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group. , (C6-C12) aryl group, -SO 2 N(R 11 )(R 12 ) or -CON(R 13 )(R 14 ), and R 11 to R 14 are independently hydrogen, (C1-C5) It is an alkyl or (C6-C12)aryl group;
Z is CR 3 or N, and R 3 is hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6-C12) It is an aryl group;
a is an integer of 0 or 1 to 5, b is an integer of 1 to 5, and a+b≤5, and when a and b are 2 or more, R 1 may be different from or the same as each other;
c is 0 or an integer from 1 to 2, and when c is 2 or more, R 2 may be different from or the same as each other;
The aryl group or heteroaryl group of Ar 1 may be substituted with one or more selected from amino group, carboxylic acid group, (C6-C12)aryl group, and -CON(R 13 )(R 14 ).
상기 화학식 1에서, R1 및 R2는 서로 독립적으로 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며,
Z는 N인 트리아진 유도체.According to clause 1,
In Formula 1, R 1 and R 2 are each independently selected from a halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1- C5) alkoxycarbonyl group or (C6-C12) aryl group,
Z is a triazine derivative where N is N.
상기 화학식 1에서 Ar1은 하기 구조식에서 선택되는 것인 트리아진 유도체.
(상기 구조식에서, R21 내지 R27은 서로 독립적으로, 아미노기, 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, -SO2N(R11)(R12) 또는 -CON(R13)(R14) 이며, R11 내지 R14는 서로 독립적으로 수소, (C1-C5)알킬 또는 (C6-C12)아릴기이며;
D1 내지 D4는 서로 독립적으로 CR15R16 또는NH이며, R15 및 R16은 서로 독립적으로 수소, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;
D5는 CR17 또는N이며, R17은 수소, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;
d는 0 또는1 내지 3의 정수이며, e는 0 또는 1 내지 6의 정수이며, f 는 0 또는 1 내지 4의 정수로, g는 0 또는 1 내지 2의 정수이며, h는 0 또는 1 내지 7의 정수이며, d, e, f, g 및 h가 2이상의 정수인 경우 각R21, R22 R24, R26 및 R27은 서로 동일하거나 상이할 수 있다.)According to clause 1,
In Formula 1, Ar 1 is a triazine derivative selected from the following structural formula.
(In the above structural formula, R 21 to R 27 are independently of each other amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (C6-C12) aryl group, -SO 2 N(R 11 )(R 12 ) or -CON(R 13 )(R 14 ), and R 11 to R 14 are independent of each other It is hydrogen, (C1-C5)alkyl or (C6-C12)aryl group;
D 1 to D 4 are each independently CR 15 R 16 or NH, and R 15 and R 16 are independently hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, or halo (C1-C5) alkyl group. , (C1-C5)alkoxycarbonyl group or (C6-C12)aryl group;
D 5 is CR 17 or N, and R 17 is hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6-C12) ) is an aryl group;
d is an integer of 0 or 1 to 3, e is an integer of 0 or 1 to 6, f is an integer of 0 or 1 to 4, g is an integer of 0 or 1 to 2, and h is 0 or an integer of 1 to 2. It is an integer of 7, and when d, e, f, g and h are integers of 2 or more, each R 21 , R 22 R 24 , R 26 and R 27 may be the same or different from each other.)
상기 화학식 1은 하기 화학식 2로 표시되는 트리아진 유도체.
[화학식 2]
[상기 화학식 2에서,
X1 및 X2는 -NH-이며;
R1 은 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, -SO2N(R11)(R12) 또는 -CON(R13)(R14)이며, R11 내지 R14는 서로 독립적으로 수소, (C1-C5)알킬 또는 (C6-C12)아릴기이며;
a 는 서로 독립적으로 0 또는 1 내지 5의 정수이며, b는 1 내지 5의 정수로, a+b≤5이며, a및 b가 2이상인 경우 R1은 서로 상이하거나 동일할 수 있으며;
Ar1은 , 또는 이며;
R21, R22 및 R27은 서로 독립적으로, 아미노기, 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기, (C6-C12)아릴기, -SO2N(R11)(R12) 또는 -CON(R13)(R14) 이며, R11 내지 R14는 서로 독립적으로 수소, (C1-C5)알킬 또는 (C6-C12)아릴기이며;
D1은 CR15R16 또는 NH이며, R15 및 R16은 서로 독립적으로 수소, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;
d는 0 또는 1 내지 3의 정수이며, e는 0 또는 1 내지 6의 정수이며, h는 0 또는 1 내지 7의 정수이며, d, e 및 h가 2이상의 정수인 경우 각 R21, R22 및 R27은 서로 동일하거나 상이할 수 있다.)According to clause 1,
The above formula (1) is a triazine derivative represented by the following formula (2).
[Formula 2]
[In Formula 2 above,
X 1 and X 2 are -NH-;
R 1 is a halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (C6-C12) Aryl group, -SO 2 N(R 11 )(R 12 ) or -CON(R 13 )(R 14 ), and R 11 to R 14 are independently hydrogen, (C1-C5)alkyl, or (C6-C12). ) is an aryl group;
a is independently 0 or an integer from 1 to 5, b is an integer from 1 to 5, and a+b≤5, and when a and b are 2 or more, R 1 may be different from or the same as each other;
Ar 1 is , or and;
R 21 , R 22 and R 27 are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) An alkoxycarbonyl group, (C6-C12)aryl group, -SO 2 N(R 11 )(R 12 ) or -CON(R 13 )(R 14 ), and R 11 to R 14 are independently hydrogen, (C1) -C5) alkyl or (C6-C12) aryl group;
D 1 is CR 15 R 16 or NH, and R 15 and R 16 are independently hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) It is an alkoxycarbonyl group or (C6-C12)aryl group;
d is 0 or an integer of 1 to 3, e is 0 or an integer of 1 to 6, h is 0 or an integer of 1 to 7, and when d, e and h are integers of 2 or more, R 21 , R 22 and R 27 may be the same or different from each other.)
상기 화학식 2에서 X1 및 X2는 -NH-이며;
R1은 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;
a는 0 또는 1 내지 5의 정수이며, b는 1 내지 5의 정수로, a+b≤5이며, a가 2 이상인 경우 R1은 서로 상이하거나 동일할 수 있으며;
Ar1은 , 또는 이며;
R21 내지 R22및 R27은 서로 독립적으로, 아미노기, 할로겐기, 니트로기, 카르복실산기, (C1-C5)알킬기, (C1-C5)알콕시기, 할로(C1-C5)알킬기, (C1-C5)알콕시카보닐기 또는 (C6-C12)아릴기이며;
D1은 NH며;
d는 0 또는 1 내지 3의 정수이며, e는 0 또는 1 내지 6의 정수이며, h는 0 또는 1 내지 7의 정수이며, d, e 및 h가 2이상의 정수인 경우 각 R21, R22 및 R27은 서로 동일하거나 상이할 수 있다.)According to clause 4,
In Formula 2, X 1 and X 2 are -NH-;
R 1 is a halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6-C12) It is an aryl group;
a is 0 or an integer from 1 to 5, b is an integer from 1 to 5, and a+b≤5, and when a is 2 or more, R 1 may be different from or the same as each other;
Ar 1 is , or and;
R 21 to R 22 and R 27 are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1) -C5) alkoxycarbonyl group or (C6-C12) aryl group;
D 1 is NH;
d is 0 or an integer of 1 to 3, e is 0 or an integer of 1 to 6, h is 0 or an integer of 1 to 7, and when d, e and h are integers of 2 or more, R 21 , R 22 and R 27 may be the same or different from each other.)
상기 안료는 부피평균입자지름이 10 내지 150nm인 안료 분산액.According to clause 8,
The pigment is a pigment dispersion having a volume average particle diameter of 10 to 150 nm.
상기 안료 분산제는 상기 안료 100중량부에 대하여, 고형분으로 10 내지 60중량부이며, 상기 안료 분산 조제는 안료 100중량부에 대하여 1 내지 25중량부를 포함하는 안료 분산액.According to clause 8,
The pigment dispersant is 10 to 60 parts by weight in solid content based on 100 parts by weight of the pigment, and the pigment dispersion aid is 1 to 25 parts by weight based on 100 parts by weight of the pigment.
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