KR20170047968A - Active energy ray-curable compositon - Google Patents
Active energy ray-curable compositon Download PDFInfo
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- KR20170047968A KR20170047968A KR1020150148730A KR20150148730A KR20170047968A KR 20170047968 A KR20170047968 A KR 20170047968A KR 1020150148730 A KR1020150148730 A KR 1020150148730A KR 20150148730 A KR20150148730 A KR 20150148730A KR 20170047968 A KR20170047968 A KR 20170047968A
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- South Korea
- Prior art keywords
- meth
- acrylate
- composition
- compound
- weight
- Prior art date
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- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
More particularly, the present invention relates to an active energy ray curable composition having an excellent elastic modulus and an elastic strain, a color filter including a spacer prepared using the active energy ray curable composition, and a liquid crystal display ≪ / RTI >
BACKGROUND ART Conventionally, (meth) acrylate has been widely used as a composition for pattern formation used in a color resist forming a colored layer of an etching resist, a solder resist and a color filter. In this case, a compound having two or more (meth) acryloyl groups (hereinafter also referred to as "multifunctional (meth) acrylate") is used for the purpose of improving the sensitivity of the composition and improving the hardness of the cured product.
That is, as a conventional composition for forming an active energy ray-curable pattern, a composition containing a polyfunctional (meth) acrylate having no carboxyl group, an alkali-soluble resin, a photopolymerization initiator and an organic solvent is known (Patent Document 1). At this time, the polyfunctional (meth) acrylate is insoluble in alkali, and a film residue of the uncured part coating film is generated at the time of development, so that sufficient resolution can not be obtained, and there is a problem that a low elastic modulus and an elastic deformation rate are obtained.
To solve this problem, there has been studied a carboxyl group-containing polyfunctional (meth) acrylate obtained by adding a compound having a hydroxyl group and a (meth) acryloyl group with a divalent or tetravalent carboxylic acid anhydride. When a compound having a hydroxyl group and a (meth) acryloyl group is reacted with a divalent or tetravalent carboxylic acid anhydride, the developing property can be partially improved through the introduction of an acid group, but not sufficient. In addition, intermolecular addition reaction occurs, resulting in additional problems such as an increase in viscosity of the composition, resulting in poor coatability, and no improvement in elastic modulus and elastic strain.
Accordingly, there is a demand for an active energy ray-curable composition which does not cause a problem such that the cured product of the composition can have an excellent elastic modulus and an elastic strain rate while increasing the viscosity.
SUMMARY OF THE INVENTION The present invention has been made in order to solve the problems of the prior art,
It is an object of the present invention to provide an active energy ray curable composition which is excellent in generally required physical properties such as hardenability, chemical resistance, heat resistance and adhesion, and is capable of ensuring elasticity and having an excellent elastic recovery rate.
It is another object of the present invention to provide a color filter including a spacer manufactured using the composition and a liquid crystal display device having the color filter.
In order to achieve the above object,
(A) having at least three (meth) acryloyl groups and hydroxyl groups and a compound in which the intramolecular hydroxyl group is Michael added to the (meth) acryloyl group of the compound Based on the total weight of the composition.
It is another object of the present invention to provide a color filter including a spacer manufactured using the composition and a liquid crystal display device having the color filter.
The active energy ray-curable composition of the present invention comprises a compound having at least three (meth) acryloyl groups and hydroxyl groups and an intra molecular Michael addition reaction compound thereof, whereby curing property, chemical resistance, etc. Not only the physical properties required in general are excellent but also the cured product can have excellent elastic modulus and elastic deformation rate.
BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 shows the shape of a side surface of a columnar spacer used for evaluation of an elastic strain rate by an electron microscope. Fig.
Fig. 2 is a production example of a compound in which a hydroxyl group in a molecule is Michael added to a (meth) acryloyl group of a hydroxy-functional (meth) acrylate.
FIG. 3 is a diagram showing a mechanism by which an intramolecular Michael-added compound including a ring structure increases the elastic strain rate.
Hereinafter, the present invention will be described in detail. In the present specification, (meth) acryl means acryl and / or methacryl, (meth) acrylate means acrylate and / or methacrylate, (meth) acryloyl means acryloyl and / Or methacryloyl.
The composition of the present invention comprises a compound (A) having three or more (meth) acryloyl groups and a hydroxyl group and a compound in which a hydroxyl group in the molecule is Michael addition to the (meth) acryloyl group of the compound B). ≪ / RTI >
Hereinafter, components constituting the active energy ray-curable composition of the present invention will be described.
(A) Three or more Meta ) Acryloyl group And Hydroxyl group Compound
The active energy ray curable composition of the present invention is a composition comprising a compound having three or more (meth) acryloyl groups and a hydroxyl group (hereinafter also referred to as a 'hydroxy-functional (meth) acrylate' or ' .
Specific examples of the hydroxyfunctional (meth) acrylate include ditrimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate and dipentaerythritol penta (meth) acrylate. Of these, pentaerythritol tri (meth) acrylate may be more preferable because of its good pattern forming ability.
The composition of the present invention may contain a compound having four or more (meth) acryloyl groups which do not have a hydroxyl group, which is a by-product in the production process, with a hydroxy polyfunctional (meth) acrylate. Examples of the compound include pentaerythritol tetra (meth) acrylate and dipentaerythritol hexa (meth) acrylate.
The component (A) and the compound having four or more (meth) acryloyl groups having no hydroxyl group may be compounded in a weight ratio of 1: 4 to 4: 1, but the present invention is not limited thereto.
Examples of the method for producing the hydroxyfunctional (meth) acrylate include a method in which (meth) acrylic acid and an alcohol are heated and stirred under an acidic catalyst. Examples of the acidic catalyst include sulfuric acid, paratoluenic acid and methanesulfonic acid. The reaction temperature can be appropriately set according to the compound to be used and the purpose, and is preferably from 70 to 140 캜. If the reaction temperature is lower than 70 ° C, the reaction is delayed. If the reaction temperature is higher than 140 ° C, the reaction system becomes unstable and impurities are formed or gelated.
As the solvent in the above-mentioned reaction, it is preferable to use an organic solvent having low solubility with water produced by the esterification reaction, and accelerate dehydration while azeotropically watering. Preferred examples of the organic solvent include aromatic hydrocarbons such as toluene, benzene and xylene; Aliphatic hydrocarbons such as hexane and heptane; And ketones such as methyl ethyl ketone and cyclohexanone. The organic solvent may be distilled off under reduced pressure after the reaction. If a solvent free from odor or the like is used, the organic solvent may be used as it is without removing to adjust the viscosity of the composition.
The alcohol used in the above reaction is a compound containing at least 4 hydroxyl groups. Specifically, polyols such as ditrimethylolpropane, pentaerythritol and dipentaerythritol, and alkylene oxide adducts of these polyols . Examples of the alkylene oxide include ethylene oxide and propylene oxide.
In addition, in the above reaction, a polymerization inhibitor may be added to the reaction solution for the purpose of preventing polymerization of the resulting (meth) acrylic acid ester. Examples of such a polymerization inhibitor include hydroquinone, hydroquinone monomethyl ether, 2,6-di-tert-butyl-p-cresol and phenothiazine.
The content of the hydroxyfunctional (meth) acrylate is preferably 10 to 80% by weight, more preferably 30 to 60% by weight based on the total weight of the solid content in the active energy ray curable composition. When the content is less than 10% by weight, the curing degree is insufficient and there is a problem that it is washed away at all during the development. When the content exceeds 80% by weight, there is a problem that pattern formation is not performed well due to overcuring. However, such a weight ratio can be appropriately adjusted depending on the purpose and use.
(B) Hydroxy Multifunctional ( Meta ) Acrylate ( Meta ) On acryloyl groups A compound in which the hydroxyl group in the molecule is Michael addition
The active energy ray curable composition of the present invention is a compound in which the hydroxyl group in the molecule is Michael addition to the (meth) acryloyl group of the hydroxyfunctional (meth) acrylate (A) ) Component ").
The component (B) may be prepared by intramolecular Michael addition reaction to the (meth) acryloyl group in the same molecule as the hydroxyl group contained in the above-mentioned hydroxy polyfunctional (meth) acrylate (Fig. 2). Such a Michael addition compound includes a ring structure. Such a ring structure functions to increase the elastic modulus and elastic strain of an active energy ray curable composition.
In more detail, when a linear compound forms a cyclic structure, the backbone rigidity is lowered and voids in the molecular ring are generated. As a result, the deformable range is expanded and the elasticity is increased So that it is easy to impart elasticity.
As the component (B), those obtained by various production methods may be used. Specifically, those produced as a by-product in the production of the component (A) may be used. That is, it is also possible to use the component (B) as a by-product when the component (A) is produced through the reaction of (meth) acrylic acid with an alcohol.
The component (B) produced during the production of the component (A) can be arbitrarily adjusted by adjusting the reaction temperature, time, kind of the component (A), equivalence ratio of reactants, or base catalyst content. But the reaction time may be 5 to 10 hours at a reaction temperature of 20 to 50 ° C, but is not limited thereto.
Alternatively, the component (B) may be synthesized separately in addition to the component (B) produced as a by-product in the production of the component (A).
In the active energy ray curable composition of the present invention, the weight ratio of the component (A) to the component (B) is preferably from 2: 1 to 10: 1, more preferably from 3: 1 to 7: 1 . When the weight ratio of the component (A) to the component (B) is within the above range, the cured product of the composition may exhibit a better elastic modulus and an elastic strain.
Here, the content of the component (A) and the component (B) was determined by high-performance liquid chromatography analysis using an inverted-phase silica column and measurement using a water / methanol-based eluent, using the calibration curve Is preferably obtained. The measurement conditions in this case include the following examples.
[High-performance liquid chromatograph analysis conditions]
- Apparatus: Toso Co., Ltd. SC-8010
- Column: ODS-100 z, manufactured by Tosoh Corporation,
Reverse phase (ODS) column (inner diameter 4.6 mm, length 250 mm). Reversed phase (ODS) silica particles with a particle diameter of 5 mu m were charged.
- 5 [mu] l of a solution of 100 mg of the composition in 10 ml of solvent is fed to the column.
- Analysis temperature: 40 ℃
- eluent: 0.015% phosphoric acid water: methanol (volume ratio) = 45:55 (Initial) -> 30:70 (30 min) -> 0: 100 (45-50 min)
- Flow rate of eluent: 1.0 ml / min
- Detection wavelength: UV 210 nm
The active energy ray-curable composition of the present invention may further contain other components than those described above, if necessary. Specifically, at least one selected from an alkali-soluble resin, a photopolymerization initiator, an organic solvent, an unsaturated group-containing compound, a pigment, a dye, a defoaming agent, a leveling agent, an inorganic filler and an organic filler. It is also possible to contain small amounts of antioxidants, light stabilizers, ultraviolet absorbers, polymerization inhibitors and the like.
Hereinafter, the alkali-soluble resin (C), the photopolymerization initiator (D) and the organic solvent (E) will be described in detail.
(C) an alkali-soluble resin
The composition of the present invention may further comprise an alkali-soluble resin (hereinafter also referred to as a 'component (C)'). The alkali-soluble resin is not particularly limited as long as it acts as a binder and is soluble in a developing solution used in a developing treatment step, particularly preferably in an alkali developing solution.
Examples of the alkali-soluble resin include an addition polymer, a polyester resin, an epoxy resin and a polyether resin, and an addition polymer obtained by polymerizing an ethylenic unsaturated monomer may be more preferable.
As the alkali-soluble resin, an alkali-soluble resin having a carboxyl group is preferable, and an ethylenically unsaturated monomer having at least one carboxyl group (hereinafter also referred to as a "carboxyl group-containing unsaturated monomer") and an ethylenically unsaturated monomer copolymerizable therewith Copolymerizable unsaturated monomer ") (hereinafter also referred to as a" carboxyl group-containing copolymer ") is preferable.
Examples of the carboxyl group-containing unsaturated monomer include unsaturated monocarboxylic acids such as (meth) acrylic acid, crotonic acid,? -Crotonic acid and cinnamic acid;
Unsaturated dicarboxylic acids or anhydrides thereof such as maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride and mesaconic acid;
An unsaturated polycarboxylic acid having three valencies or more or anhydrides thereof;
Mono [(meth) acryloyloxyalkyl] dibasic carboxylic acid such as succinic acid mono (2- (meth) acryloyloxyethyl) and phthalic acid mono (2- (meth) acryloyloxyethyl) Esters; And mono (meth) acrylates of a polymer having a carboxyl group and a hydroxyl group at both ends such as? -Carboxypolycaprolactone mono (meth) acrylate. Among these carboxyl group-containing unsaturated monomers, omega -carboxypolycaprolactone monoacrylate and phthalic acid mono (2-acryloyloxyethyl) are trade names of Aronix M-5300 and M-5400 (Donga Synthetic Co., Ltd.) And is commercially available.
These carboxyl group-containing unsaturated monomers may be used alone or in combination of two or more.
The copolymerizable unsaturated monomer is not particularly limited as long as it is copolymerizable with the carboxyl group-containing unsaturated monomer. Specific examples thereof include aromatic vinyl compounds, unsaturated carboxylic acid esters, unsaturated imides and macromonomers having a mono (meth) acryloyl group at the terminal .
Examples of the aromatic vinyl compound include styrene,? -Methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p- , 2-vinylbenzyl methyl ether, 3-vinyl benzyl methyl ether, 4-vinyl benzyl methyl ether, 2-vinyl benzyl glycidyl ether, 3-vinyl benzyl glycidyl ether, .
Examples of the unsaturated carboxylic acid esters include unsaturated carboxylic acid esters such as methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxy (Meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl Acrylate, 2-methoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, methoxy diethylene glycol (meth) acrylate, Acrylate, methoxytri Alkylene glue glycol (meth) acrylate, methoxy propylene glue glycol (meth) acrylate, methoxy dipropylene glue glycol (meth) acrylate, isobornyl (meth) acrylate, tricyclo [5.2.1.0 2, 6] (Meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate and glycerol mono (meth) acrylate.
Examples of the unsaturated imides include maleimide, N-phenylmaleimide and N-cyclohexylmaleimide.
Examples of macromonomers having a mono (meth) acryloyl group at the terminal include those having polymer molecular chains such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate and polysiloxane have.
Examples of the copolymerizable unsaturated monomer include 2- (3,4,5,6-tetrahydrophthalimide) ethyl (meth) acrylate, 2- (2,3-dimethylmaleimide) ethyl (meth) Imide (meth) acrylates such as acrylate; (Meth) acrylate, 2-aminoethyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate, 2- Unsaturated carboxylic acid aminoalkyl esters such as dimethylaminopropyl (meth) acrylate; Unsaturated carboxylic acid glycidyl esters such as glycidyl (meth) acrylate; Indene such as indene and 1-methylindene; Carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate and vinyl benzoate; Unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether; (Meth) acrylonitrile,? -Chloroacrylonitrile and vinylidene cyanide; unsaturated (meth) acrylates such as (meth) acrylamide,? -Chloroacrylamide and N-2-hydroxyethyl Amides; and aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene.
These copolymerizable unsaturated monomers may be used singly or in a mixture of at least one thereof.
Specific examples of the carboxyl group-containing copolymer include (meth) acrylic acid as an essential component, and optionally a group of succinic acid mono (2- (meth) acryloyloxyethyl), omega-carboxypolycaprolactone mono (meth) (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate and the like, and at least one compound selected from the group consisting of styrene, (Hereinafter also referred to as a " carboxyl group-containing copolymer ") is a copolymer of at least one compound selected from the group consisting of acrylate, acrylate, glycerol mono (meth) acrylate, N-phenylmaleimide, polystyrene macromonomer and polymethylmethacrylate macromonomer ).
Specific examples of the carboxyl group-containing copolymer include (meth) acrylic acid / methyl (meth) acrylate copolymer, (meth) acrylic acid / benzyl (meth) acrylate copolymer, (meth) acrylic acid / (Meth) acrylic acid / glycidyl (meth) acrylate / styrene copolymer, (meth) acrylic acid / glycidyl (meth) acrylate copolymer, (Meth) acrylate / polystyrene macromonomer copolymer, a (meth) acrylic acid / methyl (meth) acrylate / polymethyl methacrylate macromonomer copolymer, a (meth) acrylic acid / benzyl (Meth) acrylate / benzyl (meth) acrylate / polymethyl methacrylate macromonomer copolymer, (meth) acrylic acid / 2-hydroxyethyl Acrylate / polystyrene macromonomer copolymer, (meth) acrylic acid / 2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate / polymethyl methacrylate macromonomer copolymer, methacrylic acid / styrene / benzyl Styrene / benzyl (meth) acrylate / N-phenylmaleimide copolymer, (meth) acrylate / N-phenylmaleimide copolymer, (Meth) acrylate / styrene / benzyl (meth) acrylate / styrene / allyl (meth) acrylate / N-phenylmaleimide copolymers, mono [2- (meth) acryloyloxyethyl] (Meth) acrylate / glycerol mono (meth) acrylate / glycerol mono (meth) acrylate / N-phenylmaleimide copolymer and a (meth) acrylic acid / omega-carboxypolycaprolactone mono / N-phenylmale Amide copolymers and the like.
The copolymerization ratio of the carboxyl group-containing unsaturated monomer in the carboxyl group-containing copolymer is usually 5 to 50% by weight, preferably 10 to 40% by weight. In this case, when the copolymerization ratio is less than 5% by weight, the solubility of the obtained composition in an alkali developing solution tends to be lowered. When the copolymerization ratio exceeds 50% by weight, solubility in an alkali developing solution becomes excessively high, Or the pixel tends to be detached from the substrate or the surface of the spacer tends to be roughened.
As the alkali-soluble resin component in the present invention, an alkali-soluble resin having an ethylenic unsaturated group in the side chain is preferable in that the crosslinked density, film strength, heat resistance and chemical resistance of the resulting cured film are improved.
As the alkali-soluble resin having an ethylenic unsaturated group in the side chain, an alkali-soluble resin having a carboxyl group is preferable. Examples of the resin include those obtained by adding an unsaturated compound having an epoxy group (hereinafter also referred to as an " epoxy-based unsaturated compound ") to the above carboxyl group-containing copolymer.
Examples of the epoxy-based unsaturated compound include (meth) acrylates containing an epoxy group such as glycidyl (meth) acrylate and cyclohexene oxide-containing (meth) acrylate.
The addition reaction can be carried out according to a conventional method, and can be produced by adding an epoxy-based unsaturated compound to a carboxyl group-containing copolymer in an organic solvent or by using a solvent. As the condition of the addition reaction, the reaction temperature, the reaction time and the catalyst can be suitably selected according to each reaction.
The weight average molecular weight (hereinafter, also referred to as 'Mw') of the alkali-soluble resin is usually 3,000 to 300,000, preferably 5,000 to 100,000. The number average molecular weight (hereinafter also referred to as " Mn ") is usually 3,000 to 60,000, preferably 5,000 to 25,000.
In the present invention, Mw and Mn mean values obtained by converting a molecular weight measured by gel permeation chromatography (GPC, elution solvent: tetrahydrofuran) into polystyrene.
In the present invention, when such an alkali-soluble resin having a specific Mw and Mn is used, a composition having excellent developability can be obtained, whereby a pattern having a sharp pattern edge can be formed. Further, it is possible to provide an effect that residues, greasing, film residue, and the like are less likely to be generated on the substrate and the light-shielding layer of the unexposed portion during development. The ratio (Mw / Mn) of Mw to Mn may be generally 1 to 5, preferably 1 to 4.
The above-described alkali-soluble resins may be used alone or in combination of two or more.
The alkali-soluble resin is preferably contained in an amount of 10 to 70% by weight, and more preferably 10 to 40% by weight based on the total solid content in the composition of the present invention. When the content is less than 10% by weight, the film thickness after pre-baking becomes too thin. When the content exceeds 70% by weight, the viscosity of the composition becomes too high, resulting in poor coatability or excessively thick film thickness after pre-baking.
(D) Light curing Initiator
The composition of the present invention is cured by irradiation of active energy rays, and examples of the active energy ray include electron beams, visible rays, ultraviolet rays, and the like. Among these, a special device is not required, and it is preferable to use visible light or ultraviolet light because of simplicity.
In the composition of the present invention, a photopolymerization initiator (hereinafter, also referred to as a 'component (D)') is blended in a visible ray or an ultraviolet curable composition. On the other hand, in the case of an electron beam curable composition, it is not always necessary to blend a photopolymerization initiator.
Examples of the photopolymerization initiator include a photopolymerization initiator such as a biimidazole-based compound, a benzoin-based compound, an acetophenone-based compound, a benzophenone-based compound, an? -Diketone-based compound, a polynuclear quinone- Compounds and ketal-based compounds, and one or more of them can be selected and used.
Specific examples of the imidazole-based compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) Bis (2-bromophenyl) -4,4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) -1,2'-biimidazole, 2,2'- '-Bis (2-chlorophenyl) -4,4', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4-dichlorophenyl) ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4,6-trichlorophenyl) -4,4', 5,5'- Bis (2-bromophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'- Bis (2,4-dibromophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole and 2,2'-bis (2,4,6-tribromo Phenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole and the like.
When a non-imidazole-based compound is used as a photopolymerization initiator, it may be more preferable to use a hydrogen donor in combination because the sensitivity can be improved. Here, the hydrogen donor refers to a compound capable of donating a hydrogen atom to a radical generated from a non-imidazole-based compound by exposure.
As the hydrogen donor, for example, a mercaptan-based hydrogen donor and an amine-based hydrogen donor are preferable.
The mercaptan-based hydrogen donor is composed of a compound having a benzene ring or a heterocycle as a parent nucleus and having at least one, preferably 1 to 3, more preferably 1 to 2, mercapto groups directly bonded to the mother nucleus . Specific examples of the mercapan-based hydrogen donor include 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2-mercaptobenzoimidazole, 2,5-dimercapto-1,3,4-thiadiazole and 2-mercapto-2,5-dimethylaminopyridine, and the like. Of these mercaptan-based hydrogen donors, 2-mercaptobenzothiazole and 2-mercaptobenzoxazole are preferable, and 2-mercaptobenzothiazole is particularly preferable.
The amine-based hydrogen donor is composed of a compound having a benzene ring or a heterocyclic ring as a parent nucleus and having at least one, preferably 1 to 3, more preferably 1 to 2 amino groups directly bonded to the mother nucleus. Specific examples of the amine-based hydrogen donor include 4,4'-bis (dimethylamino) benzophenone, 4,4'-bis (diethylamino) benzophenone, 4-diethylaminoacetophenone, Ethyl-4-dimethylaminobenzoate, 4-dimethylaminobenzoic acid, and 4-dimethylaminobenzonitrile.
The hydrogen donors may be used alone or in combination of two or more. However, the spacers or pixels formed by using one or more kinds of mercaptan-based hydrogen donors in combination with one or more amine-based hydrogen donors are difficult to be removed from the substrate at the time of development , The spacer or the pixel is high in strength and sensitivity. Also, a hydrogen donor having both a mercapto group and an amino group can be preferably used.
Specific examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin i-propyl ether, benzoin i-butyl ether and methyl 2-benzoyl benzoate.
Specific examples of the acetophenone-based compound include 2,2-dimethoxyacetophenone, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2-hydroxy- Methyl-1- [4- (methylthio) phenyl] -2-morpholin-2- (4-morpholinophenyl) -2-methyl-2-hydroxypropan-1-one, 1- -Benzyl-2-dimethylaminobutan-1-one, 1-hydroxycyclohexyl phenyl ketone and 2,2-dimethoxy-1,2-diphenylethan-1-one.
Specific examples of the benzophenone-based compound include benzyldimethylketone, benzophenone, 4,4'-bis (dimethylbenzophenone), and 4,4'-bis (diethylbenzophenone).
Specific examples of the? -diketone-based compound include diacetyl, dibenzoyl, methylbenzoylformate and the like.
Specific examples of the polynuclear quinone-based compound include anthraquinone, 2-ethyl anthraquinone, 2-t-butyl anthraquinone, and 1,4-naphthoquinone.
Specific examples of the xanthone-based compound include xanthone, thioxanthone, and 2-chlorothioxanthone.
Specific examples of the triazine compound include 1,3,5-tris (trichloromethyl) -s-triazine, 1,3-bis (trichloromethyl) -5- (2'-chlorophenyl) (Trichloromethyl) -5- (4'-chlorophenyl) -s-triazine, 1,3-bis (trichloromethyl) (Trichloromethyl) -5- (4'-methoxyphenyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, 2- (4-ethoxystyryl) -4,6-bis (trichloromethyl) -s -Triazine and 2- (4-n-butoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine.
Among them, 1-hydroxycyclohexyl phenyl ketone or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane- And is preferably used in the invention.
One or more of the photopolymerization initiators may be selected and used.
The photopolymerization initiator is preferably used in an amount of 0.5 to 20 parts by weight based on 100 parts by weight of solid components other than the photopolymerization initiator in the composition. When the amount is less than 0.5 part by weight, the photocuring property may be insufficient. When the amount is more than 20 parts by weight, the exposed part may be easily broken during alkali development.
The content of the photopolymerization initiator is preferably 1 to 30% by weight, more preferably 1 to 20% by weight based on the total weight of the solid content in the composition. When the content is within the above-mentioned range, it is more preferable because a pattern with high precision can be obtained.
(E) Organic solvents
In the present invention, an organic solvent (hereinafter also referred to as "component (E)") may further be added to the composition for the purpose of improving the applicability of the composition. The organic solvent may be any one that does not react with each component of the composition. Further, an organic solvent having a boiling point of 80 to 200 캜 is preferable from the viewpoint of excellent coatability and a drying rate of the obtained coating film, and an organic solvent having a boiling point of 100 to 170 캜 is more preferable.
Specific examples thereof include aromatic compounds such as toluene and xylene; Fatty acid esters such as butyl acetate, benzyl acetate, propylene glycol monomethyl ether acetate and ethoxyethyl propionate; Cellosolves such as ethyl cellosolve and butyl cellosolve; Alkylene glycol ethers such as propylene glycol monomethyl ether; Alcohols such as ethanol, ethylene glycol and diethylene glycol; Ethers such as diethylene glycol dimethyl ether; Ketones such as methyl isobutyl ketone and cyclohexanone; Formamide such as N, N-dimethylformamide; lactam such as? -butyrolactam and N-methyl-2-pyrrolidone; And lactones such as? -Butyrolactone.
The organic solvent may be used alone or in combination of two or more.
The content of the solvent is preferably 50 to 90% by weight based on the total weight of the composition of the present invention, which is preferable in terms of good coatability.
The composition of the present invention can be used for various purposes. For example, a composition for pattern formation such as a resist, a coating material such as an ink and a coating material, and the like can be given. Among them, the composition of the present invention can be suitably used as a composition for forming a pattern.
Since the composition of the present invention has a high exposure sensitivity and is excellent in the elastic modulus and the elastic deformation rate after curing, plastic deformation of the pattern hardly occurs, and a precise and precise pattern can be formed. Therefore, it can be preferably used as a composition for forming an active energy ray-curable pattern.
When the composition of the present invention is used as a composition for pattern formation, a composition containing the components (A), (B), (C), (D) and (E) is preferable.
As a pattern forming method using the above composition, a composition may be applied to a substrate and dried to form a coating film. Then, an active energy ray is irradiated thereon through a mask having a specific pattern shape to cure the coating film, And a method of developing the cured portion with a developing solution.
Examples of the substrate include glass and plastic. As the developing solution, an alkaline developing solution is preferable, and concrete examples are as shown later.
As the composition for forming a pattern, resists such as etching resists and solder resists, columnar spacers in the production of liquid crystal panels, coloring compositions for forming pixels and black matrices in color filters, and color filter protective films can be given.
The composition of the present invention can be preferably used for columnar spacers in the production of liquid crystal panels among these applications.
In the case of using as a columnar spacer, a nonionic surfactant such as polyoxyethylene lauryl ether or a fluorine surfactant may be added to the composition in order to improve coatability and developability. Alternatively, an adhesive preparation, a storage stabilizer, a defoaming agent, and the like may be appropriately added as necessary.
Hereinafter, the use of columnar spacers (hereinafter also referred to as "spacers") will be described.
Spacer
The spacer is formed by the photocured coating film of the composition by a photolithography method. The spacers can be formed in arbitrary sizes at arbitrary positions in a liquid crystal panel substrate, but are often formed on a black matrix region or a TFT electrode, which is generally a light shielding portion of a color filter.
The spacer may be formed according to a conventional method. For example, the composition of the present invention may be applied on a substrate such as glass to a thickness required for forming a cell gap, and then heated (hereinafter also referred to as "prebaking" , A method of drying the coating film and forming the coating film through exposure, development, and post-heating (hereinafter, also referred to as post-baking).
When the composition is applied on a substrate, it is applied to a slightly larger thickness of the cell gap in consideration of reduction and deformation of the film due to development, post-baking, and the like. Concretely, it is preferable that the film thickness after pre-baking is 5 to 10 탆, more preferably 6 to 7 탆.
Examples of the application method include a printing method, a spraying method, a roll coating method, a bar coating method, a curtain coating method, a spin coating method and a die coating method (slit coat method) Die coating method is used.
After the composition is applied onto the substrate, pre-baking is performed. In this case, the temperature and time conditions for prebaking may be about 5 to 15 minutes at 50 to 150 ° C. Light is irradiated through a mask having a predetermined pattern shape for forming a spacer on the coated film surface after prebaking.
The light used is preferably ultraviolet light or visible light, and wavelength light of 240 to 410 nm obtained from a high-pressure mercury lamp or a metal halide lamp may be used.
The light irradiation conditions are preferably such that the light irradiation amount is generally from 50 to 600 mJ / cm < 2 > although it depends on the type of the light source, the absorption wavelength of the photopolymerization initiator used or the film thickness of the coating film. If the irradiation amount is less than 50 mJ / cm < 2 >, the exposed portion tends to be detached at the time of development due to defective curing. If the irradiation amount exceeds 600 mJ / cm < 2 >, a precise spacer pattern tends to be difficult to obtain.
After irradiating the coating film surface with light, the unexposed portion is removed by a developer.
As the developer, an aqueous solution of an alkaline compound can be used. Examples of the alkaline compound include potassium hydroxide, sodium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate, ammonia, tetramethylammonium hydroxide, and the like. In order to accelerate the developing rate, a water-soluble organic solvent such as methanol, ethanol, isopropanol, and benzyl alcohol or various surfactants may be added in an appropriate amount to the developing solution.
The developing method may be any one selected from a puddle method, a dipping method and a spraying method. After development, the pattern portion is cleaned with water for 0.5 to 1.5 minutes, and is dried by air with compressed air or the like to obtain a spacer pattern. The obtained spacer pattern is post-baked by a heating device such as a hot plate or oven at a temperature of 150 to 350 占 폚 to obtain a liquid crystal panel spacer of the present invention.
The post baking can volatilize the residual solvent and moisture absorbed at the time of development, and can improve the heat resistance of the spacer. Though the thickness of the spacer varies depending on the cell gap set value of the liquid crystal panel, it is designed so as to be 3 to 5 μm after post-baking.
When the composition of the present invention is used in the production of a spacer, compression of a planar indenter (indenter formed with a plane of 100 m x 100 m) at room temperature is measured using an ultra-small microhardness tester (H-100C available from Fisher Instruments Co., It is preferable that the elastic deformation ratio [(elastic deformation ratio / total amount of displacement) x 100] measured under the condition that the load becomes 0.2 GPa is 60% or more.
That is, the active energy ray-curable composition of the present invention can be preferably used for producing a spacer, and provides a color filter including the spacer.
Further, the present invention provides a liquid crystal display device provided with the color filter.
Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. However, the following examples illustrate the present invention and the present invention is not limited by the following examples, and various modifications and changes may be made. The scope of the present invention will be determined by the technical idea of the following claims.
< Manufacturing example >
Manufacturing example One. Acrylate Preparation of compounds
100 g (0.735 mol) of pentaerythritol and 160 g (2.22 mol) of acrylic acid as a raw material were dissolved in 200 g of propylene glycol monomethyl ether (PGME), followed by stirring at 80 ° C. 5 g of triethylamine as a catalyst and 0.5 g of 2,5-bis (1,1,3,3-tetramethylbutyl hydrocue) (DOHQ) as a polymerization inhibitor were added and the esterification reaction was carried out at 90 ° C. for 3 hours Respectively.
Thus, a compound a1 having three or more (meth) acryloyl and hydroxyl groups and a compound b1 having a hydroxyl group in the molecule added to the (meth) acryloyl group in a1 were obtained.
Manufacturing example 2. Acrylate Preparation of compounds
The reaction was carried out in the same manner as in Preparation Example 1, except that the esterification reaction was carried out for 6 hours.
As a result, a hydroxy-functional acrylate a2 having at least one hydroxyl group and a compound b2 in which a hydroxyl group in the molecule was added to the (meth) acryloyl group in a2 was prepared.
TMPTA: trimethylpropane triacrylate (Shin Nakamura)
The other components in Table 1 may be the unreacted reactant, the cross-linked polymeric material, or the like.
< Synthetic example >
Synthetic example 1. Synthesis of alkali-soluble resin
A separable flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel and a nitrogen-introducing tube was charged with 52 parts by weight of methyl methacrylate, 23 parts by weight of acrylic acid, diethylene glycol dimethyl ether (hereinafter referred to as "DMDG" 5 parts by weight of 2,2'-azobis (2-methylbutyronitrile) was added to the total weight of the monomers (100 parts by weight), and the components were homogeneously dissolved. Thereafter, the mixture was stirred at 85 DEG C for 2 hours under a nitrogen stream, and then reacted at 100 DEG C for 1 hour. To the obtained solution, 25 parts by weight of glycidyl methacrylate, 10 parts by weight of triethylamine with respect to glycidyl methacrylate, 1 part by weight of hydroquinone with respect to glycidyl methacrylate, DMDG was further added so that the combined weight of glycidyl methacrylate was 35% by weight, and the mixture was stirred at 100 占 폚 for 5 hours to obtain a desired copolymer solution (solid content concentration: 31.5%).
The Mw of the obtained alkali-soluble resin was 22,000, the acid value was 84 mgKOH / g, and the hydroxyl value was 96 mgKOH / g.
< Example 1 to 3 and Comparative Example 1 to 3>
Were mixed in the composition shown in Table 2 below to prepare a curable composition. The contents of Table 1 above may be reflected for some components contained in the composition of Table 2 below.
castle
water
Alkali-soluble resin
Photopolymerization initiator I-907: 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, IRGACURE 907 manufactured by Ciba Specialty Chemicals
Solvent DMDG: Diethylene glycol dimethyl ether
TMPTA: trimethylpropane triacrylate (Shin Nakamura)
< Experimental Example >
Experimental Example 1. Elasticity Strain rate evaluation
A composition shown in Table 2 was coated on a chromium mask glass substrate of 10 cm square by a spin coater and the coating film was dried for 10 minutes by an air dryer at 80 占 폚 to form a coating film having a dry film thickness of 6 占 퐉. A photomask was arranged at a distance of 100 mu m from this coating film, and ultraviolet rays were irradiated with a proximity aligner at an intensity of 300 mJ / cm 2 (365 nm in terms of illuminance) by ultrahigh pressure mercury or the like. Subsequently, the substrate was immersed in a 0.5 wt% sodium carbonate aqueous solution at a liquid temperature of 23 DEG C for 60 seconds to undergo alkali development to remove only the uncured portion of the coating film. Thereafter, the substrate was allowed to stand in an atmosphere at 200 占 폚 for 30 minutes to carry out heat treatment to form a columnar spacer having a height of 5 占 퐉 and a diameter of 10 to 20 占 퐉.
The elastic strain rate of the obtained columnar spacer at room temperature was measured using a micro-hardness tester (H-100C, manufactured by Fisher Instruments Co., Ltd.) equipped with a planar indenter (indenter with a plane of 100 m x 100 m) (Elastic deformation amount / total displacement amount) x 100] under the condition that the load becomes 0.2 GPa.
Experimental Example 2. Shape evaluation
The ratio (S2 / S1) of the area (S2) measured by observing the columnar spacers used for the evaluation of the elastic strain rate by an electron microscope and the lower limit (S1) was calculated (see FIG. When this value exceeds 100, it means that the elastic deformation rate is easily lowered because it becomes a reverse tapered phase.
As can be seen from Table 3, all of Examples 1 to 3 exhibited an excellent elastic deformation rate of 70% or more and a sufficient elastic deformation rate for a spacer or a protective film. The shape evaluation result was also confirmed to be less than 100% and no reverse taper phase was observed.
On the other hand, in the case of Comparative Examples 1 to 3 which did not contain a cyclic compound in which the hydroxyl group in the molecule was Michael added to the (meth) acryloyl group of the hydroxyfunctional (meth) acrylate of the present invention, the elastic deformation rate was 40% , And the result of the shape evaluation exceeded 100%, indicating that an inverse tapered phase was observed and the elastic strain rate was likely to be lowered.
Claims (7)
With respect to the total weight of solids in the composition,
And 10 to 80% by weight of a compound having at least three (meth) acryloyl groups and at least one hydroxyl group.
The compound (A) having at least three (meth) acryloyl groups and hydroxyl groups and the compound (B) having Michael addition of the intramolecular hydroxyl group in the (meth) acryloyl group : 1 to 10: 1, based on the total weight of the composition.
Further comprising at least one member selected from the group consisting of an alkali-soluble resin (C), a photopolymerization initiator (D), and an organic solvent (E).
With respect to the total weight of solids in the composition,
10 to 70% by weight of an alkali-soluble resin and
Further comprising 1 to 30% by weight of a photopolymerization initiator,
About the total weight of the composition
And 50 to 90% by weight of an organic solvent.
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