KR20140019112A - Thermosetting ink composition, thermosetting material manufactured by using the thermosetting ink composition and display device having the thermosetting material - Google Patents
Thermosetting ink composition, thermosetting material manufactured by using the thermosetting ink composition and display device having the thermosetting material Download PDFInfo
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- KR20140019112A KR20140019112A KR1020120085433A KR20120085433A KR20140019112A KR 20140019112 A KR20140019112 A KR 20140019112A KR 1020120085433 A KR1020120085433 A KR 1020120085433A KR 20120085433 A KR20120085433 A KR 20120085433A KR 20140019112 A KR20140019112 A KR 20140019112A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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Abstract
The present disclosure relates to a thermosetting ink composition, and more particularly, to a thermosetting ink composition comprising a crosslinking agent including a blocked isocyanate group, a binder resin including an acid group or a hydroxyl group, a thermosetting ink composition including a colorant and a solvent. It is about.
Description
The present specification relates to a thermosetting ink composition having a high degree of curing and chemical resistance and capable of low temperature baking using an ink composition including a compound including a blocked isocyanate group.
A fine pattern of a color filter used in a display device such as a liquid crystal display device or a plasma display panel is usually formed by photolithography using a negative photoresist, (Develop) -firing (Curing) process. The pattern formed by the development in the firing step is cured by baking for 20 to 30 minutes at a high temperature of 220 ℃ to 230 ℃ using a convection oven (convection oven).
Currently, display manufacturers are making great efforts to shorten the process time by improving the photolithography process, and recently, in order to shorten the process time, using infrared rays (IR), 1 minute at a high temperature of 250 ° C or 280 ° C The high-temperature fast curing to be fired for 5 to 5 minutes, or the rapid hardening for 2 to 3 minutes using microwave (Microwave) has been progressed. However, in the case of IR curing, even if the time is shortened, it may occur due to deterioration of the material because it proceeds at a high temperature of 250 ° C, and it is difficult to ensure uniformity of IR curing as the substrate size increases. In the case of hardening using microwaves, not only the specific functional groups capable of absorbing and vibrating microwaves of a specific wavelength must be sufficiently contained in the material used in the pattern, and the material is also processed at high temperature. Problems may occur due to deterioration.
In particular, in order to improve the contrast ratio, brightness, and color reproduction of liquid crystal display products, dyes other than conventional pigments are used, or one of the next-generation displays is applied to a flexible display using a plastic substrate instead of a glass substrate. In view of the heat resistance of the dye or the heat resistance of the plastic substrate after the pattern formation, a low temperature of 190 ° C., preferably 150 ° C. or lower is essential.
An object of the present specification is to provide a thermosetting ink composition having high curing degree and chemical resistance and capable of low temperature baking.
In order to achieve the above object, the present disclosure provides a thermosetting ink composition comprising a binder resin, a colorant and a solvent comprising a block isocyanate compound, an acid group or a hydroxyl group.
In addition, there is provided a thermoset made of the thermosetting ink composition.
Also, a display device including the thermosetting material is provided.
Thermosetting ink composition according to one embodiment of the present specification has the advantage of having a high degree of curing and chemical resistance.
Thermosetting ink composition according to an exemplary embodiment of the present specification has the advantage that low-temperature baking is possible.
1 is a graph showing the deblocking of a blocked isocyanate group over time of a compound of formula 8 at 150 ° C.
2 is a graph showing deblocking of a blocked isocyanate group over time in a composition comprising a compound represented by the general formula (8) and a binder resin at 150 캜.
FIG. 3 is a graph comparing the change in area of C = N peak with time in the graphs of FIG. 1 and FIG. 2;
In order to achieve the above object, the present specification provides a thermosetting ink composition comprising a binder resin, a colorant and a solvent comprising a block isocyanate compound, an acid group or a hydroxyl group.
Hereinafter, the present specification will be described in more detail.
The said block isocyanate type compound is a compound containing a blocked isocyanate group, If an isocyanate group is blocked, it will not specifically limit.
For example, the dimer, trimer or polyisocyanate of an aliphatic or aromatic diisocyanate can be selected from the group consisting of alcohol, phenol, caprolactam, oxime, pyrazole, pyrazole, malonate, or the like can be used as the blocking agent.
For example, the block isocyanate compound may be represented by the following general formula (1).
[Formula 1]
In Formula 1,
G is H, an alkyl group having 1 to 3 carbon atoms, an acrylate group, -NCO,
In this case, E1, E2 and E3 are each independently a direct bond or substituted or unsubstituted C 1 ~ C 10 Alkylene.
X is substituted or unsubstituted C 1 -C 10 alkylene; Substituted or unsubstituted C 3 -C 30 cycloalkylene; Substituted or unsubstituted C 3 -C 30 heterocyclo alkylene; Substituted or unsubstituted C 6 -C 20 arylene; Or substituted or unsubstituted C 6 ~ C 20 heteroarylene,
n is an integer of 1 to 3.
Where G is
A is any one of the following Chemical Formulas 2 to 7,
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
[Formula 7]
In Chemical Formulas 2 to 7,
R 1, R 2, R 3, R 4,
The alkylene group (alkylene, -C n H 2n - ) is an alkane (alkane, C n H 2n + 2) is missing, one of the hydrogen atoms on the carbon atoms form the ends of, cycloalkylene (cycloalkylene, -C n H 2n- 2- (n≥3)) is a form in which one hydrogen atom is missing from a carbon atom at both ends of a cycloalkane (C n H 2n ). In addition, the arylene is in the form of one hydrogen atom missing from one of the carbon atoms at both ends of the aromatic ring, may include one or more aromatic rings, the two or more ring systems may be present in the form of bonding or fusion with each other.
In Formula 1 of the present specification, the C 1 ~ C 10 alkylene is -CH 2- , -CH 2 CH 2- , -CHCH 3 CH 2- , -CH 2 CH 2 CH 2- , -CH 2 CH 2 CH 2 CH 2- , -CH (CH 2 CH 3 ) CH 2- , -CH (CH 3 ) CH 2- , -CH (CH 2 CH 2 CH 3 )-, -CH 2 (CHCH 3 CH 3 )-, -CH 2 CH 2 CH 2 CH 2 CH 2- , -CH (CH 3 ) CH 2 CH 2 CH 2- , -CH 2 CH (CH 3 ) CH 2 CH 2- , -CH (CH 3 ) CH 2 CH (CH 3 ) —, —CH (CH 3 ) CH (CH 3 ) CH 2 —. -CH 2 CH 2 CH (CH 2 CH 3 )-, -CH 2 CH (CH 2 CH 3 ) CH 2- , -CH (CH 3 ) CH (CH 2 CH 3 )-, -CH 2 CH (CH 2 CH 2 CH 3 )-, -CH 2 CH (CHCH 3 CH 3 )-, -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2- , -CH 2 CH 2 CH 2 CH 2 CH (CH 3 )-, -CH 2 CH 2 CH 2 CH (CH 3 ) CH 2- , -CH 2 CH 2 CH (CH 3 ) CH 2 CH 2- , -CH (CH 2 CH 3 ) CH 2 CH 2 CH 2- , -CH 2 CH (CH 2 CH 3 ) CH 2 CH 2- , -CH (CH 3 ) CH (CH 3 ) CH 2 CH 2- , -CH (CH 3 ) CH 2 CH (CH 3 ) CH 2- , -CH (CH 3 ) CH 2 CH 2 CH (CH 3 )-, -CH 2 CH (CH 3 ) CH 2 CH (CH 3 )-, -CH 2 CH (CH 3 ) CH (CH 3 ) CH 2 -,- CH 2 CH 2 CH (CH 2 CH 2 CH 3 )-, -CH 2 CH 2 CH (CHCH 3 CH 3 )-, -CH 2 CH (CH 2 CH 2 CH 3 ) CH 2- , -CH 2 CH ( CH 2 CH 3 CH 3 ) CH 2- , -CH (CH 2 CH 2 CH 2 CH 3 ) CH 2- , -CH (CH 2 CHCH 3 CH 3 ) CH 2- , -CH (CHCH 3 CH 2 CH 3 ) CH 2- , -CH (CCH 3 CH 3 CH 3 ) CH 2- , -CH (CH 2 CH 2 CH 3 ) CH (CH 3 )-, -CH (CHCH 3 CH 3 ) CH (CH 3 )- , -CH (CH 2 CH 2 CH 2 CH 2 CH 3 )-, -CH (CH 2 CH 2 CHCH 3 CH 3 )-, -CH (CH 2 CCH 3 CH 3 CH 3 )-, -CH (CCH 3 CH 3 CH 2 CH 3) - , -CH (CH 2 CHCH 3 CH 2 CH 3) -, -CH (CHCH 3 CHCH 3 CH 3) - such as linear But the number of branched alkyl renil, and the like.
In Formula 1 of the present specification, the C 3 ~ C 30 cyclo alkylene may include cyclo propylene, cyclo butylene, cyclo pentylene, cyclo hexylene, cyclo heptylene, cyclo octylene, but is not limited thereto. no.
In Formula 1 of the present specification, the C 6 ~ C 20 Arylene is a phenyl group (phenyl group), tolyl group (tolyl group), biphenyl group (biphenyl group), pentalenyl group (pentalenyl group), indenyl group (indenyl group) ), Naphthyl group, biphenylylenyl group, anthracenyl group, anthracenyl group, azulenyl group, heptarenyl group, acenaphthylenyl group , Phenenalyl group (phenalenyl group), fluorenyl group (fluorenyl group), methyl anthryl group, phenanthrenyl group, triphenylenyl group pyrenyl group, chrysenyl group, ethyl- chrysenyl group (ethyl-chrysenyl at the carbon atoms at one end of the group, perylenyl group, methyl anthryl, phenanthrenyl group, triphenylenyl group, pyrenyl group It may include one or more aromatic rings missing one hydrogen atom, but is not limited thereto. No.
In Formula 1 of the present specification, the C 1 ~ C 3 Alkyl group may include -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , -CHCH 3 CH 3 , but is not limited thereto.
The heterocyclo alkylene and hetero arylene are those in which at least one carbon of cycloalkylene and arylene is substituted with N, S or O, respectively.
When the alkylene, cyclo alkylene, heterocyclo alkylene, arylene or heteroarylene is substituted with additional substituents, their substituents are -F, -Cl, -Br, -CN, -NCO, -COOH, It may be selected from the group consisting of —NO 2 , —NH 2 , —OH, —CH 3 , —CH 2 CH 3 and —CHCH 2 CH 2 , but is not limited thereto.
Of the substituents of Formula 1 A is an OH-, -OCH 3, -COOCH 3, -CN, halogen, or -NH 2 nucleophilic groups that can attract the hydrogen atoms bonded to N at a certain temperature , And the blocked isocyanate group of the compound of Formula 1 can be activated by a deblocking reaction in which the nucleophilic group attracts hydrogen atoms bonded to nitrogen at a certain temperature.
The block isocyanate compound may be used as a crosslinking agent in a thermosetting ink composition.
As described above, the block isocyanate-based compound represented by the formula (1) has a deblocking reaction in which the nucleophilic group of A in the substituent of the formula (1) at a certain temperature pulls hydrogen atoms bonded to nitrogen in the block isocyanate The isocyanate group of the crosslinking agent can be activated.
The activated isocyanate group of the crosslinking agent may react with a binder resin containing an acid group or a hydroxy group to be described later to form a crosslink.
The block isocyanate compound may be included in an amount of 2 to 50 parts by weight based on 100 parts by weight of solids in the thermosetting ink composition.
When the content of the crosslinking agent including the blocked isocyanate group is less than 2 parts by weight with respect to 100 parts by weight of the solid content of the thermosetting ink composition, the amount of isocyanate groups that may react with the acid groups or the hydroxyl groups of the binder resin is small so that the degree of curing decreases. If the content is more than 50 parts by weight, the content of the binder resin that can form a matrix may be reduced, thereby decreasing the physical properties.
In addition, the content of the block isocyanate compound is 0.5 to 20 parts by weight based on 100 parts by weight of the total thermosetting ink composition.
In the present specification, a binder resin including an acid group or a hydroxyl group capable of reacting with an isocyanate group of the crosslinking agent activated by a diblocking reaction may be used.
In order to introduce an acid group or a hydroxyl group into the binder resin, one or more polymers may be selected from a group consisting of a monomer including an acid group, a monomer including a hydroxy group, and a monomer capable of copolymerizing with a monomer containing an acid group or a hydroxyl group. Can be.
Monomers containing the acid group include (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, isoprene sulfonic acid, styrene sulfonic acid, 5-norbornene-2-carboxylic acid, and 2-((meth) acrylo Yloxy) ethyl phthalate, 2-((meth) acryloyloxy) ethyl succinate, ω-carboxy polycaprolactone mono (meth) acrylate, 2-acryloyloxyethyl succinate, 2-acryloyloxy One or more selected from the group consisting of ethyl phthalate, 2-acryloyloxyethyl hexahydrophthalate, ε-carboxy polycaprolactone monoacrylate, and the like can be used alone or in combination.
Examples of the monomer containing a hydroxy group include hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, and 4-hydroxybutyl (meth). ) Acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylic It can be used individually or in mixture of 1 or more types chosen from the group which consists of a rate and butyl (alpha)-hydroxymethyl acrylate, etc.
The monomer copolymerizable with the monomer containing the acid group or the hydroxyl group is one selected from the group consisting of unsaturated carboxylic acid esters, aromatic vinyls, unsaturated ethers, unsaturated imides, N-vinyl tertiary amines, and maleic anhydrides. The above can be used.
Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl ( Meta) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydroperpril (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylic Latex, methoxy tripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, p-nonyl phenoxy polyethylene Recall (meth) acrylate, p-nonylphenoxy polypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3, One selected from the group consisting of 3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate and tribromophenyl (meth) acrylate Can be.
Specific examples of the aromatic vinyl system include styrene,? -Methylstyrene, (o, m, p) -vinyltoluene, (o, m, p) -methoxystyrene, and (o, ≪ / RTI >
Specific examples of the unsaturated ether system may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether.
Specific examples of the unsaturated imide system include, but are not limited to, selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide Lt; / RTI >
Specific examples of the N-vinyl tertiary amines may be selected from the group consisting of N-vinyl pyrrolidone, N-vinyl carbazole, and N-vinyl morpholine.
Specific examples of the maleic anhydride type include maleic anhydride or methyl maleic anhydride, but are not limited thereto.
When the carboxyl group is included in the monomer including the acid group, the acid group or the hydroxy group is included through the reaction of the carboxyl group in the monomer and the epoxy group of glycidyl (meth) acrylate in the monomer copolymerizable with the monomer including the acid group or the hydroxy group. The polymerizable acrylate group can be further introduced into the side chain of the binder resin.
It is preferable that the molar ratio of the acid in the said binder resin and the blocked isocyanate group in a crosslinking agent is 3: 1-1: 3.
The acid value of the binder resin containing the acid group or the hydroxyl group is preferably in the range of 50 to 200 KOH mg / g. When the acid value is less than 50 KOH mg / g, the reactivity may be decreased due to the lack of functional groups capable of reacting with the isocyanate group generated by the deblocking reaction. When the acid value of the resin exceeds 200 , The content of other monomers in the binder resin is decreased, and heat resistance and the like can be reduced.
The weight average molecular weight of the binder resin containing an acid group or a hydroxyl group is preferably in the range of 1,000 to 200,000, more preferably in the range of 3,000 to 30,000.
When the weight average molecular weight of the binder resin is less than 1000, the binding function between the components required as the binder polymer is weak, and the physical properties such as basic heat resistance and chemical resistance required for the color filter pattern cannot be satisfied, and the weight average molecular weight exceeds 200,000. In this case, the viscosity of the polymer is greatly increased, so that the viscosity of the ink composition is also greatly increased, and the flowability is also deteriorated, making it difficult to control the coating thickness or to secure thickness uniformity.
The binder resin including the acid group or the hydroxyl group is preferably contained in an amount of 2 to 50 parts by weight based on 100 parts by weight of the solid content in the thermosetting ink composition.
When the content of the binder resin containing an acid group or a hydroxyl group is less than 2 parts by weight, the resin may form a matrix due to a low content of the resin capable of forming the matrix, and when it exceeds 50 parts by weight, the viscosity of the ink composition may also be reduced. It is greatly increased and the flowability is also worse, making it difficult to control the coating thickness or to ensure thickness uniformity.
The content of the binder resin including the acid group or the hydroxyl group is 1 to 20 parts by weight based on 100 parts by weight of the total thermosetting ink composition.
The thermosetting ink composition provided herein may include a colorant for exhibiting color characteristics. The colorant may be selected from the group consisting of a red pigment, a violet pigment, a blue pigment, a green pigment, a yellow pigment, an orange pigment, a black pigment and a carbon black.
The red pigments used to show the color characteristics used in the preparation of the ink include naphthol-based red pigments Pig.Red # 1 (CI12070), Pig.Red # 2 (CI12310), Pig.Red # 3 (CI 12120), Pig.Red # 4 (CI12085), Pig.Red # 5 (CI12490), Pig.Red # 6 (CI12090), Pig.Red # 7 (CI12420), Pig.Red # 8 (CI 12355), Pig.Red # 9 (CI12460), Pig.Red # 10 (CI12440), Pig.Red # 11 (CI12430), Pig.Red # 12 (CI12385), Pig.Red # 13 (CI 12395), Pig.Red # 14 (CI12380), Pig.Red # 15 (CI12465), Pig.Red # 16 (12500), Pig.Red # 17 (CI12390), Pig.Red # 18 (CI12350 ), Pig.Red # 21 (CI12300), Pig.Red # 22 (CI12315), Pig.Red # 23 (CI12355), Pig.Red # 31 (12360), Pig.Red # 32 (12320), Pig.Red # 95 (CI15897), Pig.Red # 112 (CI12370), Pig.Red # 114 (CI12351), Pig.Red # 119 (CI12469), Pig.Red # 146 (CI12485), Pig.Red # 147 (CI12433), Pig.Red # 148 (CI12369), Pig.Red # 150 (CI12290), Pig.Red # 151 (CI15890), Pig.Red # 184 (CI12487), Pig.Red # 187 (CI12486), Pig.Red # 188 (CI12467), Pig.Red # 210 (CI12474), Pig.Re d # 245 (C.I.12317), Pig.Red # 253 (C.I.12375), Pig.Red # 258 (C.I.12318), Pig.Red # 261 (C.I.12468); Pig.Red # 49 (CI15630), Pig.Red # 49: 1 (CI15630: 1), Pig.Red # 49: 2 (CI15630: 2), Pig.Red # 49: naphthol-based and metal complexes 3 (CI15630: 3), Pig.Red # 50: 1 (CI15500: 1), Pig.Red # 51: 1 (CI15580: 1), Pig.Red # 53 (CI15585), Pig.Red # 53: 1 (CI15585: 1), Pig.Red # 68 (CI15525), Pig.Red # 243 (CI15910), Pig.Red # 247 (CI15915); Disazo pyrazolones such as Pig.Red # 37 (C.I.21205), Pig.Red # 38 (C.I.21210), Pig.Red # 41 (C.I.21200); Disazo condensates Pig.Red # 144 (CI 20735), Pig.Red # 166 (CI20035), Pig.Red # 220 (CI20055), Pig.Red # 221 (CI20065), Pig.Red # 242 (CI20067); Pig.Red # 48: 1 (CI15865: 1), Pig.Red # 48: 2 (CI15865: 2), Pig.Red # 48: 3 Pig.Red # 48: 4 (CI15865: 4), Pig.Red # 48: 5 (CI15865: 5), Pig.Red # 52: # 52: 2 (CI15860: 2), Pig.Red # 57: 1 (CI15850: 1), Pig.Red # 58: 4 (CI15880: 2), Pig.Red # 64 (CI15800), Pig.Red # 64: 1 (CI15880: 1), Pig.Red # 63 15800: 1), Pig.Red # 200 (CI15867); Pig.Red # 60: 1 (CI.16105: 1), Pig.Red # 66 (CI.18000: 1), Pig.Red # 67 (CI.18025: 1), which are metal complexes of naphthalene sulfonic acid; Pig.Red # 81: 1 (C.I.45160: 1), Pig.Red # 81: 3 (C.I.45160: 3), Pig.Red # 169 (C.I. Pig.Red # 89 (C.I. 60745), Pig.Red # 177 (65300), which is an anthraquinone system; Pig.Red # 88 (C.I.73312), Pig.Red # 181 (C.I.73360), which are ciiodigo-based; The quinacridone family Pig.Red # 122 (C.I.73915), Pig.Red # 207 (C.I.73900), Pig.Red # 209 (C.I.73905); (CI71145), Pig.Red # 149 (CI71137), Pig.Red # 178 (CI71155), Pig.Red # 179 (CI71130), Pig.Red # 190 71140), Pig.Red # 194 (CI71100), Pig.Red # 224 (CI71127); (CI12512), Pig.Red # 175 (CI12513), Pig.Red # 176 (CI12515), Pig.Red # 185 (CI12516), Pig.Red # 208 (CI 12514); Pyranthrone Pig.Red # 216 (C.I.59710); Diketopyrrolopyrrolidone Pig.Red # 254 (C.I.56110); And Pig.Red # 260 (C.I.56295), which is isoindolin-based, and the like.
As a violet pigment, Pig.Violet # 1 (CI45170: 2), Pig.Violet # 2 (CI45175: 1), Pig.Violet # 3 (CI42535: 2) and Pig.Violet # 27 which are triaryl carbonium (CI42535: 3), Pig.Violet # 39 (CI42555: 2); Anthraquinone system Pig.Violet # 5: 1 (C.I.58055: 1); Naphthol-based Pig.Violet # 25 (C.I.12321), Pig.Violet # 50 (C.I.12322); Pig.Violet # 19 (C.I.73900) which is a quinacridone family; Pig.Violet # 23 (C.I.51319) and Pig.Violet # 37 (C.I.51345), which are dioxazines; Perylene-based Pig.Violet # 29 (C.I.71129); And benzimidazolone-based Pig.Violet # 32 (C.I.12517).
As the blue pigment, Pigment Blue # 15: 6, which is a triarylcarbonium-based pigment, Pig.Blue # 1 (CI42595: 2), Pig.Blue # 2 (CI44045: 2), Pig.Blue # 9 (CI42025: 1), Pig.Blue # 10 (CI44040: 2), Pig.Blue # 14 ( CI42600: 1), Pig.Blue # 18 (CI42770: 1), Pig.Blue # 19 (CI42750), Pig.Blue # 56 (CI42800), Pig.Blue # 62 (CI44084); Cu phthalocyanine-based Pig.Blue # 15 (CI74160), Pig.Blue # 15: 1 (CI74160); Pig.Blue # 16 (CI74100), which is a metal-free phthalocyanine series; Indanthrone system Pig.Blue # 60 (CI69800), Pig.Blue # 64 (CI69825); And Pig.Blue # 66 (CI73000), Pig.Blue # 63 (CI73015: x), and the like which are indigo based.
Pig.Green # 1 (C.I.42040: 1), Pig.Green # 2 (C.I.42040: 1), Pig.Green # 4 (C.I. Pig.Green # 7 (C.I.74260), Pig.Green # 36 (C.I.74265), Cu phthalocyanine series; And Pig.Green # 8 (C.I.10006), Pig.Green # 10 (C.I.12775), which are metal complexes, and the like.
Yellow pigments include monoazo pigments Pig.Yellow # 1 (CI11680), Pig.Yellow # 2 (CI11730), Pig.Yellow # 3 (CI11710), Pig.Yellow # 5 (CI11660), Pig.Yellow # 6 (CI11670), Pig.Yellow # 10 (CI12710), Pig.Yellow # 49 (CI11765), Pig.Yellow # 65 (CI11740), Pig.Yellow # # 74 (CI11741), Pig.Yellow # 75 (CI11770), Pig.Yellow # 97 (CI11767), Pig.Yellow # 98 (CI11727), Pig.Yellow # 111 # 116 (CI 11790), Pig Yellow # 167 (CI 11737); Pig.Yellow # 61 (CI13880), Pig.Yellow # 62: 1 (CI13940: 1), Pig.Yellow # 100 (CI19140: 1), Pig.Yellow # 168 ), Pig.Yellow # 169 (CI13955), Pig.Yellow # 183 (CI18792); Pig.Yellow # 16 (C.I.20040), a bisacetoacetarylide system; (CI21090), Pig.Yellow # 13 (CI21100), Pig.Yellow # 14 (CI21095), Pig.Yellow # 17 (CI21105), Pig.Yellow # 55 CI21096), Pig.Yellow # 63 (CI21091), Pig.Yellow # 81 (CI21127), Pig.Yellow # 83 (CI21108), Pig.Yellow # 87 (CI21107: 113 CI21126, Pig.Yellow # 114 CI21092, Pig.Yellow # 124 CI21107, Pig.Yellow # 126 CI21101, Pig.Yellow # 127 21102, Pig.Yellow # 152 (CI21111), Pig.Yellow # 170 (CI21104), Pig.Yellow # 171 (CI21106), Pig.Yellow # 172 (CI21109), Pig.Yellow # 174 (CI21098); Pig.Yellow # 24 (C.I.70600), which is a flavones system; Diazo condensates Pig.Yellow # 93 (CI20710), Pig.Yellow # 94 (CI20038), Pig.Yellow # 95 (CI20034), Pig.Yellow # 128 (CI20037), Pig.Yellow # 166 CI20035); Anthraquinone system Pig.Yellow # 123 (C.I.65049), Pig.Yellow # 147 (C.I.60645); Pig.Yellow # 101 (C.I.48052), aldina; Pig.Yellow # 104 (CI.15985: 1), a naphthalenesulfonic acid metal complex; Pigra Yellow # 108 (C.I.68420), which is anthrapyrimidine; Pig.Yellow # 110 (C.I.56280), Pig.Yellow # 139 (C.I.56298), Pig.Yellow # 185 (C.I.56290), which are isoindolinone systems; Pig.Yellow # 154 (CI13980), Pig.Yellow # 175 (CI11784), Pig.Yellow # 180 (CI21290), Pig.Yellow # 181 (CI 11777); And quinophthalone-based Pig.Yellow # 138 (C.I.56300); Pig.Yellow # 117 (CI48043), Pig.Yellow # 129 (CI48042), Pig.Yellow # 150 (CI12764), Pig.Yellow # 153 (CI48545), Pig.Yellow # 177 (CI) 48120), Pig. Yellow # 179 (CI48125), and the like.
In addition, orange pigments include Piga Orange # 1 (C.I.11725), Pig.Orange # 6 (C.I.12730), which are monoazo; Naphthol-based Pig.Orange # 2 (CI12060), Pig.Orange # 5 (CI12075), Pig.Orange # 22 (CI12470), Pig.Orange # 24 (CI12305), Pig.Orange # 38 (CI12367 ); Pig.Orange # 17 (CI15510: 1 Pig.Orange # 17: 1 (15510: 2), Pig.Orange # 46 (CI15602), which is a naphthol metal complex, Pig.Orange # 13 Pig.Orange # 19 (CI15990) which is a naphthalenesulfonic acid metal complex, Pig.Orange # 16 (CI21160), Pig.Orange # ; Pig.Orange # 31 (CI20050) which is a disazo-based condensate; Pig.Orange # 36 (CI11780), Pig.Orange # 60 (CI11782) Pig.Orange # 48 (CI73900), which is a quinacridone system, and Pig.Orange # 61 (CI11265), which is an isoindoline system, Pig.Orange # 66 (CI48210), Pig.Orange # 69 (CI56292), and the like.
The colorant containing a black pigment can be used by mixing carbon black with two or more colored pigments. Examples of the carbon black include CISTO 5HIISAF-HS, CISTO KH, CISTO 3HHAF-HS, CISTO NH, CISTO 3M, CISTO 300HAF-LS, CISTO 116HMMAF-HS, CISTO 116MAF , Cysto FMFEF-HS, Cysto SOFEF, Cysto VGPF, Cysto SVHSRF-HS, and Cysto SSRF; Diagram Black II, Diagram Black N339, Diagram Black SH, Diagram Black H, Diagram LH, Diagram HA, Diagram SF, Diagram N550M, Diagram M, Diagram E, Diagram G, Diagram R, Diagram N760M, Diagram LR, # 2700, # 2600, # 2400, # 2350, # 2300, # 2200, # 1000, # 980, # 900, MCF88, # 52, # 50, # 47, # 45, # 45L, CF9, # 95, # 3030, # 3050, MA7, MA77, MA8, MA11, OIL7B, OIL9B, OIL11B, OIL30B, and OIL31B; PRINTEX-55, PRINTEX-55, PRINTEX-45, PRINTEX-35, PRINTEX-55, PRINTEX-85, PRINTEX-75, PRINTEX- SPECIAL BLACK-350, SPECIAL BLACK-250, SPECIAL BLACK-100, and LAMP BLACK-101; PRINTEX-25, PRINTEX-200, PRINTEX-40, PRINTEX-30, PRINTEX-3, PRINTEX-A; SPECIAL BLACK-550; And RAVEN-1100ULTRA, RAVEN-1080ULTRA, RAVEN-1060ULTRA, RAVEN-1040, RAVEN-1035, RAVEN-1020, RAVEN-1000, RAVEN-890H, RAVEN-890, RAVEN-880ULTRA, RAVEN-860ULTRA , RAVEN-850, RAVEN-820, RAVEN-790ULTRA, RAVEN-780ULTRA, RAVEN-760ULTRA, RAVEN-520, RAVEN-500, RAVEN-460, RAVEN-450, RAVEN-430ULTRA, RAVEN-420, RAVEN-410, RAVEN -2500ULTRA, RAVEN-2000, RAVEN-1500, RAVEN-1255, RAVEN-1250, RAVEN-1200, RAVEN-1190ULTRA, RAVEN-1170, and the like.
Examples of colorants usable in combination with the carbon black include carmine 6B (CI12490), phthalocyanine green (CI 74260), phthalocyanine blue (CI 74160), Mitsubishi carbon black MA100, perylene black (BASF K0084.K0086) LINOL YELLOW (CI 21090), LINOL YELLOW GRO (CI 21090), Benzidine Yellow 4T-564D, Mitsubishi Carbon Black MA-40, Victoria Pure Blue (CI 42595) PIGMENT RED97, 122, 149, 168, 177, 180, 192, 215, C.I. PIGMENT GREEN 7, 36, C.I. PIGMENT 15: 1, 15: 4, 15: 6, 22, 60, 64, C.I. PIGMENT 83, 139 or C.I. PIGMENT VIOLET 23, etc. In addition, a white pigment or a fluorescent pigment may be used. The coloring agent may be used alone or in combination of two or more so that the color thereof becomes black.
The colorant may be used alone or in combination of two or more thereof, and it is preferable that the colorant is included in an amount of 10 to 60 parts by weight based on 100 parts by weight of the solid content in the thermosetting ink composition according to the required color, color characteristics, and film characteristics.
When the amount of the colorant is less than 10 parts by weight, the coloring property of the ink composition may not be sufficiently exhibited. When the amount of the coloring agent is more than 60 parts by weight, the amount of the crosslinking agent including the binder resin and the blocked isocyanate group may be relatively decreased, have.
In addition, the content of the colorant is 1 to 10 parts by weight based on 100 parts by weight of the total thermosetting ink composition.
The thermosetting ink composition of the present specification includes a solvent, and the solvent may be used alone or in combination of two or more in consideration of solubility, pigment dispersibility, and coatability.
The solvent is propylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, cyclohexanone, 2-heptanone, 3-heptanone, 2-hydroxyethylpropionate, 3-methyl-3-methoxybutylpropionate, ethyl-3-methoxypropionate, methyl-3-ethoxypropionate, ethyl-3-ethoxypropionate Nate, Butyl Acetate, Amyl Permate, Isoamyl Acetate, Isobutyl Acetate, Butyl Propionate, Isopropyl Butyrate, Ethyl Butyrate, Butyl Butyrate, Ethyl Pyruvate, γ-Butyrol Acetate, Methyl Ethyl Ketone, Methyl Cellosolve , Ethyl cellosolve, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, Pylene glycol diethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, 2-ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, 3-methoxy Butyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, ethyl acetate, propyl acetate or dipropylene glycol monomethyl ether, and the like, but not limited thereto. It doesn't happen.
The content of the solvent is 50 to 90 parts by weight based on 100 parts by weight of the total thermosetting ink composition.
The thermosetting ink composition provided herein may further include a polyfunctional monomer having an ethylenically unsaturated double bond, a thermal polymerization initiator, a surfactant, and other additives.
The multifunctional monomer having an ethylenically unsaturated double bond may be selected from the group consisting of trimethylol ethane triacrylate, trimethylol propane triacrylate, neopentyl glycol (meth) acrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, di Pentaerythritol pentaacrylate, and the like. Other multifunctional monomers that can be used include epoxy acrylates of bisphenol A derivatives, novolac-epoxy acrylates, and urethane-based polyfunctional acrylates such as U-324A, U15HA, or U -4HA and the like can be used. The polyfunctional monomer which has the said ethylenically unsaturated double bond can also be used individually or in mixture of 2 or more types.
The polyfunctional monomer having an ethylenically unsaturated double bond is preferably used in an amount of 0 to 50 parts by weight based on 100 parts by weight of the total solid of the thermosetting ink composition, and the content of the polyfunctional monomer having an ethylenically unsaturated double bond is 50 parts by weight. When exceeded, the content of the compound containing the block isocyanate group is reduced, so that the effect of low temperature firing is greatly reduced, thereby greatly reducing the degree of curing during low temperature firing, and greatly weakening the physical properties of the film.
The content of the polyfunctional monomer having an ethylenically unsaturated double bond is 0 to 20 parts by weight based on 100 parts by weight of the total thermosetting ink composition.
The thermal polymerization initiator may be an azo-based compound such as Wako Pure Chemical Industris. Azo nitrile-based V-60, V-65, V-59, V-70, V-40; V-601 which is an azo ester system; Azo amide based VA-086, VA-085, VA-080, Vam-110, Vam-111, VF-096; Azo amidine-based V-50, VA-044, VA-046B, Aam-027, VA-060, VA-057, VA-061; And macroazo initiators VPS-0501, VPS-1001, VPE-0201, VPE-0401, VPE-0601, VPTG-0301, etc. may be further used, but are not limited thereto.
The thermal polymerization initiator is preferably included in 0 to 5 parts by weight based on 100 parts by weight of the solid content of the thermosetting ink composition. When the thermal polymerization initiator is more than 5 parts by weight, an excess thermal polymerization initiator may be used to reduce the solubility in the ink, thereby generating a precipitate or greatly reducing the storage stability.
The content of the thermal polymerization initiator is 0 to 1 parts by weight based on 100 parts by weight of the total thermosetting ink composition.
In addition, the surfactant may be a silicone-based surfactant or a fluorine-based surfactant. Specifically, the silicone-based surfactant is BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK-310, BYK-320, BYK-322 by BYK-Chemie. , BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK-354, BYK-355, BYK-356, BYK -358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, or BYK-390, and the like, and fluorine-based surfactants such as F-114, manufactured by DIC (DaiNippon Ink & Chemicals) F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F- 472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF1132, TF1027SF, TF- 1441 or TF-1442 can be used, but is not limited thereto.
The surfactant is preferably used 0.02 to 1 parts by weight based on 100 parts by weight of the total thermosetting ink composition. When the content of the surfactant is less than 0.02 parts by weight, it is easy to occur when the coating does not proceed smoothly due to poor leveling or wetting properties of the ink coating, and when it is more than 1 part by weight, the surfactant is used excessively. Problems such as poor defoaming may occur.
As the other additives, at least one of a curing accelerator, a plasticizer, an adhesion promoter, a filler, a coupling agent, a dispersant, and the like may be used, but the present invention is not limited thereto.
Examples of the curing accelerator include F-475 (Dai Nippon Ink & Chemicals), 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2- mercaptobenzoxazole, (3-mercaptopropionate), pentaerythritol tris (3-mercaptopropionate), pentaerythritol (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), trimethylolpropane tris (2-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate), trimethylolethane Tris (2-mercaptoacetate), and trimethylolethane tris (3-mercaptopropionate).
The coupling agent may be 3-methacryloxypropyltrimethoxysilane, and the dispersing agent may be a polyester dispersing agent or the like, but is not limited thereto.
The curing accelerators, plasticizers, adhesion promoters, fillers, coupling agents or dispersants may be used as those generally known in the art.
The content of the other additives is 0.01 to 5 parts by weight based on 100 parts by weight of the total thermosetting ink composition.
The present specification provides a thermoset made of a thermosetting ink composition.
Although the thermosetting ink composition of the present specification is preferably used for a color filter of a thin film transistor liquid crystal display device, a black matrix, an overcoat layer, a column spacer of a thin film transistor liquid crystal display device or an organic light emitting diode, paints, inks, adhesives, printing plates, printing It can also be used for manufacturing wiring boards, other transparent cured products, and plasma display panels, and the use thereof is not particularly limited.
The present specification provides a display device including a thermoset.
The display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), a thin film transistor. The liquid crystal display device may be any one of a liquid crystal display (LCD-TFT) and a cathode ray tube (CRT).
The present specification provides a color filter manufactured using the thermosetting ink composition.
The color filter may be manufactured by a method known in the art, except for using the thermosetting ink composition according to the present specification.
Specifically, a black matrix is formed on the transparent substrate by coating a metal film such as chromium or a black resin film and patterning the same by a photolithography method to form a black matrix as a boundary other than the pixel region where the color filter is formed.
A pattern is formed using the thermosetting ink composition according to the present invention having red, green, and blue color in a pixel region defined by transparent openings between partition walls, and is cured to form red, green, and blue color filters. Can be.
The color filter according to the present disclosure may include a binder polymer and a thermosetting ink composition in a molar ratio of 1: 3 to 1: 5, and may include a thermal polymerization initiator and a surfactant together to prevent occurrence of a film difference.
In addition, the present specification provides a liquid crystal display device including the color filter.
The method of manufacturing the liquid crystal display device according to the present specification may use techniques in the art, except for using the thermosetting ink composition of the present specification.
The present specification will be described in more detail with reference to the following examples. However, the examples are provided to illustrate the present specification and the scope of the present specification is not limited thereto.
Example One
The low-temperature curing type blue ink contains 2.44 parts by weight of Pigment Blue # 15: 6, 1.20 parts by weight of Pigment Violet # 23 as a colorant, benzyl (meth) acrylate, N-phenylmaleimide, styrene 8.25 parts by weight of a copolymer (Mw = 7,500, AV 125) in which styrene and (meth) acrylic acid were formed in a molar ratio of 50:10:10:30, a trimer-blocked isocyanate (TPA- 2.26 parts by weight (B 2 OX, Asahi KASEI. LTD.) (Molar ratio of acrylic acid in the binder resin to blocked isocyanate in the cross-linking agent is 2: 1), 0.06 part by weight of F-475 (DaiNippon Ink & Chemicals) 0.07 parts by weight of 3-methacryloxypropyltrimethoxysilane as a coupling agent, 3.29 parts by weight of a polyester-based dispersant as a dispersant, and 82.43 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed, and the mixture was stirred for 5 hours for thermosetting. An ink composition was prepared.
[Formula 8]
Example 2
6.80 parts by weight of the resin binder of Example 1 and a trimer-blocked isocyanate (TPA-B80X, Asahi KASEI. 1) of the resin binder of Example 1 so that the molar ratio of acrylic acid in the binder resin and the blocked isocyanate in the crosslinking agent is 1: 1. LTD) 3.71 parts by weight was used, and other components were prepared in the same manner as in Example 1 to prepare a thermosetting ink composition.
Example 3
5 parts by weight of the resin binder of Example 1 and 5.51 parts by weight of the trimer-blocked isocyanate (TPA-B80X, Asahi KASEI. LTD.) With a crosslinking agent so that the molar ratio of acrylic acid in the binder resin and the blocked isocyanate in the crosslinking agent is 1: 2. Other components were used in the same manner as in Example 1 to prepare a thermosetting ink composition.
Example 4
Blocked isocyanate (E402-B80T, Asahi KASEI. LTD.) Represented by the following formula (9) with 7.33 parts by weight of the resin binder of Example 1 and a crosslinking agent so that the molar ratio of acrylic acid in the binder resin and the blocked isocyanate in the crosslinking agent is 1: 1. 4.18 parts by weight was used, and other components were prepared in the same manner as in Example 1 to prepare a thermosetting ink composition.
[Chemical Formula 9]
Comparative Example One
4.23 parts by weight of the resin binder of Example 1 and 6.28 parts by weight of bisphenol A type epoxy resin (LER148, Hexion Korea, epoxy equivalent 180 eq / g) as a crosslinking agent were used. Curable blue ink was prepared.
Experimental Example
Evaluation of Chemical Resistance of Ink Composition
The following method was used to test the chemical resistance of the thermosetting ink composition prepared according to the present specification.
Each of the thermosetting ink composition solutions prepared by Examples 1 to 3 and Comparative Example 1 was spin coated on glass, pre-baked at about 90 ° C. for 100 seconds, and then again. The film was formed by post-bake at 150 ° C. for about 30 minutes.
The chemical resistance of each thermosetting ink composition was cut out of the color coating film formed on the glass substrate by 5 cm x 2 cm by the method described above and soaked in 16 g of 80 ° C. N-methyl pyrrolidone (NMP) for 40 minutes, followed by spectrophotometer ( UV-vis spectrometer) was used to measure the absorbance of the N-methyl pyrrolidone solution in which the pigment was eluted. The lower the absorbance, the smaller the amount of the eluted pigment.
The results of the chemical resistance test are shown in Table 1 below.
[Table 1] Measurement results of chemical resistance of low temperature calcined color ink composition
Claims (12)
[Chemical Formula 1]
In Formula 1,
G is H, an alkyl group having 1 to 3 carbon atoms, an acrylate group, -NCO,
E1, E2 and E3 are each independently a direct bond or a substituted or unsubstituted C 1 ~ C 10 Alkylene,
X is substituted or unsubstituted C 1 -C 10 alkylene; Substituted or unsubstituted C 3 -C 30 cycloalkylene; Substituted or unsubstituted C 3 -C 30 heterocyclo alkylene; Substituted or unsubstituted C 6 -C 20 arylene; Or substituted or unsubstituted C 6 ~ C 20 heteroarylene,
n is an integer of 1 to 3,
A is any one of the following Chemical Formulas 2 to 7,
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
(7)
In Chemical Formulas 2 to 7,
R 1, R 2, R 3, R 4, R 5, R 6 and R 7 are each independently H, an alkyl group having 1 to 3 carbon atoms, an aryl group having 6 to 20 carbon atoms. -OH, -OCH 3 , -COOCH 3 , -CN, a halogen group or -NH 2 .
Monomers containing the hydroxy group include hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, and 4-hydroxybutyl (meth). Acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate And at least one selected from the group consisting of butyl α-hydroxymethyl acrylate.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160096241A (en) * | 2015-02-04 | 2016-08-16 | 삼성디스플레이 주식회사 | Display device and manufacturing method thereof |
| KR20160139985A (en) * | 2015-05-29 | 2016-12-07 | 동우 화인켐 주식회사 | Low-temperature thermosetting composition for printing, flexible color filter and method for preparing flexible color filter using the same |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160096241A (en) * | 2015-02-04 | 2016-08-16 | 삼성디스플레이 주식회사 | Display device and manufacturing method thereof |
| US9676162B2 (en) | 2015-02-04 | 2017-06-13 | Samsung Display Co., Ltd. | Display device and manufacturing method thereof |
| KR20160139985A (en) * | 2015-05-29 | 2016-12-07 | 동우 화인켐 주식회사 | Low-temperature thermosetting composition for printing, flexible color filter and method for preparing flexible color filter using the same |
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