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WO2019093827A1 - Copolymère ayant une propriété photodurcissable et thermodurcissable, et composition de résine photosensible, film de résine photosensible, et filtre coloré l'utilisant - Google Patents

Copolymère ayant une propriété photodurcissable et thermodurcissable, et composition de résine photosensible, film de résine photosensible, et filtre coloré l'utilisant Download PDF

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Publication number
WO2019093827A1
WO2019093827A1 PCT/KR2018/013652 KR2018013652W WO2019093827A1 WO 2019093827 A1 WO2019093827 A1 WO 2019093827A1 KR 2018013652 W KR2018013652 W KR 2018013652W WO 2019093827 A1 WO2019093827 A1 WO 2019093827A1
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Prior art keywords
group
carbon atoms
meth
photosensitive resin
repeating unit
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PCT/KR2018/013652
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English (en)
Korean (ko)
Inventor
박혜진
조창호
안정애
오미연
손경철
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LG Chem Ltd
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LG Chem Ltd
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Priority claimed from KR1020180136598A external-priority patent/KR102118627B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to JP2019553075A priority Critical patent/JP6911272B2/ja
Priority to CN201880032826.2A priority patent/CN110709435B/zh
Publication of WO2019093827A1 publication Critical patent/WO2019093827A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • 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
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/56—Acrylamide; Methacrylamide
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
    • 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
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate

Definitions

  • the present invention relates to a copolymer having photo-curable properties and thermosetting properties, a photosensitive resin composition using the same, a photosensitive resin film, and a color filter. More specifically, the present invention relates to a thermosetting resin composition which has an excellent thermosetting property at a relatively low temperature and can proceed with photo-curing by light irradiation, and has a photocurable property and a thermosetting property capable of having excellent durability, , A photosensitive resin composition using the same, a photosensitive resin film, and a color filter.
  • the photosensitive resin composition is coated using a spin or a slit coater, pre-baked, exposed, and developed.
  • a final post-baking process of 220 ° C or more is carried out.
  • Generally used glasses do not deform at this temperature, but they can be applied to flexible displays.
  • the plastic used has a problem that severe deformation occurs at a temperature of 220 ° C or higher.
  • the present invention provides a copolymer having photo-curability and thermosetting property which can have excellent durability, chemical resistance and storage stability through layered curing, which has an excellent thermosetting property at a relatively low temperature and can proceed with photo-curing by light irradiation .
  • the present invention also provides a photosensitive resin composition, a photosensitive resin film, and a color filter using the copolymer having the photocurable and thermosetting properties.
  • a first (meth) acrylate repeating unit in which an organic functional group including an epoxy group is bonded to a branched chain terminal; And a second (meth) acrylate repeating unit in which an organic functional group including an alkenyl group is bonded to the branched chain terminal, wherein in the second (meth) acrylate repeating unit, the branch chain has a substitution An alkyl ester group having 1 to 20 carbon atoms; Or an oxyalkyl ester group having 1 to 20 carbon atoms substituted with a hydroxy group; Or an alkyl ester group substituted by a cycloalkyl group having 3 to 30 carbon atoms in which the hydroxy group is substituted; Or a multi-GLA alkyl ester group having 7 to 30 carbon atoms substituted with a hydroxy group; Or an alkyl ester group substituted by a multicyclic alkyloxy group having 7 to 30 carbon atoms substituted with a hydroxy group.
  • the present specification also includes copolymers having the photocurable and thermosetting properties described above; A photopolymerizable monomer having at least two photocurable unsaturated functional groups; And a photo-initiator.
  • the present invention also includes: 1) coating the photosensitive resin composition on a substrate to form a coating film; 2) drying the coating film; 3) irradiating the dried coating film with light to cure the coating; And 4) thermosetting the photocured film at 50 ° C to 250 ° C.
  • a manufacturing method is provided.
  • the present specification also includes copolymers having the photocurable and thermosetting properties described above; And a photopolymerizable monomer having two or more photocurable avidity functional groups.
  • a color filter including the above photosensitive resin film.
  • a component when referred to as “ comprising ", it means that it can include other components, aside from other components, unless specifically stated otherwise.
  • substituted means that a different functional group is bonded in place of a hydrogen atom in a compound, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, , Two or more substituents may be the same as or different from each other.
  • (meth) acryl may mean acryl or methacryl.
  • the weight average molecular weight refers to the weight average molecular weight in terms of polystyrene measured by the GPC method.
  • a detector such as a known analyzer and a refractive index detector may be used, and a column for analysis may be used.
  • the silver condition, solvent, f low rat e can be applied.
  • the evaluation temperature is 160 ° C using a Waters PL-GPC220 instrument using a Polymer Laboratories PLeg MIX-B 300 osmagnetic column and 1, 2, 4-trichlorobenzene Was used as a solvent.
  • the flow rate was adjusted to a flow rate of ImL / min, the sample was adjusted to a concentration of 10 mg / lOmL, and the solution was supplied in an amount of 200 iiL.
  • the value of Mw was determined using a calibration curve formed using polystyrene standards .
  • the molecular weight of the polystyrene standards was 2,000 I 10,000 I 30,000 I 70,000 I 200,000 I 700,000 / 2,000,000 / 4,000,000 / 10,000,000.
  • the alkyl group is a monovalent functional group derived from an alkane, for example, straight, branched or cyclic, and includes methyl, ethyl, propyl, isobutyl, secbutyl, tert -Butyl, pentyl, or novolac.
  • One or more hydrogen atoms included in the alkyl group may be substituted with another substituent.
  • substituents examples include an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyl group having 6 to 10 carbon atoms An aryl group having 2 to 12 carbon atoms, a heteroaryl group having 2 to 12 carbon atoms, an arylalkyl group having 6 to 12 carbon atoms, a halogen atom, a cyano group, an amino group, an amidino group, a nitro group, an amide group, a carbonyl group, A methine group, and an alkoxy group having 1 to 10 carbon atoms.
  • the cycloalkyl group is not particularly limited, and examples thereof include monovalent functional groups derived from monocyclic cycloalkane. Examples thereof include, but are not limited to, preferably 3 to 60 carbon atoms, , The cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another state, the number of carbon atoms of the cycloalkyl group is 3-6.
  • cyclopropyl examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- , 4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.
  • the multi-ring alkyl group is not particularly limited, but is a monovalent functional group derived from a polycyclic cycloalkane.
  • examples thereof include, but are not particularly limited to, preferably 3 to 60 carbon atoms,
  • the cycloalkyl group has 3 to 30 carbon atoms.
  • Specific examples thereof include, but are not limited to, Nor bornane, 2,3-tr imethylenenorbornane, and the like.
  • the aryl group is a monovalent functional group derived from arene
  • monocyclic or polycyclic may be a phenyl group, a biphenyl group, a terphenyl group, a stilbenyl group, or the like, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group, a fluorenyl group, and the like, but is not limited thereto.
  • At least one hydrogen atom in each of these aryl groups may be substituted with the same substituent as in the case of the alkyl group.
  • the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl,
  • an alkylene group is a divalent functional group derived from an alkane, and has 1 to 20, or 1 to 10, or 1 to 5 carbon atoms.
  • it may be a straight chain, branched or cyclic group such as a methylene group, an ethylene group, a propylene group, an isobutylene group, a sec-butylene group, a tert-butylene group, a pentylene group and a nuclear silicone group.
  • the at least one hydrogen atom contained in the lower alkylene group may be substituted with the same substituent as in the case of the above alkyl group.
  • the oxyalkylene group is a functional group derived from the alkylene group and has a structure in which an ether group (-O-) is bonded to one terminal of the alkylene group, and the number of carbon atoms is 1 to 20, or 1 to 10, or 1 To 5.
  • the hydrocarbon group include straight chain, branched or cyclic groups such as an oxymethylene group, an oxyethylene group, an oxypropylene group, an oxy n-butylene group, an oxyisobutylene group, an oxy sec-butylene group, A pentylene group, an oxyhexylene group and the like.
  • the at least one hydrogen atom contained in the oxyalkylene group may be substituted with the same substituent as in the case of the alkyl group.
  • the cycloalkylene group is a divalent functional group derived from cycloalkane and has 3 to 30 carbon atoms, or 3 to 20 carbon atoms, or 3 to 10 carbon atoms.
  • cyclic olefins examples include cyclopentylene, cyclopentylene, cyclopentylene, 3-methylcyclopentylene, 2,3-dimethylcyclopentylene, cyclohexylene, 3-methylcyclohexylene, 4-methylcyclohexylene, But are not limited to, 3-dimethylcyclonucleosilane, 3,4,5-trimethylcyclohexylsilane, 4-tert-butylcyclonucleosilane, cycloheptylene, cyclooctylene and the like.
  • the multi-ring alkylene group means a divalent functional group derived from a multi-ring alkane, which is a polycyclic cycloalkane, in which one hydrogen atom has been substituted with a functional group in the multi-middle alkyl group.
  • the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 30 carbon atoms.
  • the compound may be a compound having the following structure. .
  • the ester group may be substituted with a straight-chain, branched or cyclic alkyl group or a multi-ring alkyl group having 1 to 25 carbon atoms in the ester group.
  • the ester group substituted with the alkyl group may be referred to as an " alkyl moiety group ", and the ester moiety substituted with the polyhydric allyl group may be referred to as a " multi-ring alkyl ester group ".
  • a resin composition comprising: a first (meth) acrylate repeating unit having a branched functional group bonded to a branched functional group containing an epoxy group; And at the branched end (Meth) acrylate repeating unit in which an organic functional group including an alkenyl group is bonded, and in the second (meth) acrylate repeating unit, the branched chain is an alkyl ester group having 1 to 20 carbon atoms substituted with a hydroxy group ; Or an alkyl ester group substituted by a cycloalkyl group having 3 to 30 carbon atoms in which a hydroxy group is substituted; Or a multicyclic alkyl ester group having 7 to 30 carbon atoms substituted with a hydroxy group; Or an alkyl ester group substituted by a multicyclic alkyloxy group having 7 to 30 carbon atoms in which the hydroxyl group has been substituted can be provided.
  • an organic functional group containing an alkenyl group contained in the repeating unit of (meth) The photo-curing can be carried out to form a primary curing structure, and an organic functional group including an epoxy group contained in the repeating unit of (meth) acrylate can be thermally cured at a low temperature of less than 200 ° C to form a secondary As the cured structure is formed, sufficient curing can proceed by thermal curing and light curing at low temperatures.
  • the photopolymerizable and thermosetting copolymers may include a first (meth) acrylate repeating unit having an organic functional group including an epoxy group bonded to the branched chain terminal.
  • (Meth) acrylate repeating unit the epoxy group contained in the first (meth) acrylate repeating unit can form a cured structure through thermal curing even at a temperature of less than 200 ° C .
  • a chain formed through the double bond-containing reaction of (meth) acrylate is referred to as a main chain, and a chain branched from the main chain Branched chain or side chain.
  • the repeating unit of the (meth) acrylate is a repeating unit contained in the homopolymer of the (meth) acrylate monomer, and the repeating unit of the main chain (meth) acrylate monomer May contain an ester functional group contained in a polyethylene chain or a branched (meth) acrylate monomer by polymerization of a vinyl group contained in the polymer. That is,
  • the branch chain terminal at which the organic functional group including the epoxy group is combined can terminate the ester functional group contained in the (meth) acrylate repeating unit.
  • the branched chain may be a carbonyl group (-C0-) or an alkyl ester group having 1 to 20 carbon atoms (R 'COO-; R' is an alkyl group having 1 to 20 carbon atoms); Or an oxyalkyl ester group having 1 to 20 carbon atoms;
  • the organic functional group including the epoxy group may be bonded to the terminal of the carbonyl group or the alkyl group having 1 to 20 carbon atoms contained in the alkyl ester group having 1 to 20 carbon atoms.
  • the organic functional group including the epoxy group may include a functional group composed of only an epoxy group or a functional group having an epoxy group bonded to another organic functional group, and specifically includes a functional group represented by the following formula (1); Or a functional group represented by the following formula (2); Or a functional group represented by the following formula (3).
  • R 1; R 2 and R 3 may each independently be a direct bond, hydrogen, or an alkyl group having 1 to 5 carbon atoms, and preferably R 2 and R 3 may be two hydrogen atoms.
  • I ⁇ and ⁇ each independently represents a direct bond or an alkylene group having 1 to 5 carbon atoms, preferably a carbon A methylene group of a number of 1, and an ethylene group of 2 carbon atoms.
  • R 1 and R 2 are each independently a direct bond or an alkylene group having 1 to 5 carbon atoms, and X is a direct bond, -O-, or -S-.
  • repeating unit of the system 1 (meth) acrylate may be represented by the following formula (4).
  • each of 3 ⁇ 4 to R 10 is independently hydrogen or an alkyl group having 1 to 10 carbon atoms, and the total number of carbon atoms in the alkylene group is 1 to 20,
  • Ru is an organic functional group including an epoxy group.
  • 3 ⁇ 4 and R 10 are each independently hydrogen
  • R 7 is an alkyl group having 1 to 3 carbon atoms
  • R is any one of a direct bond and an alkylene group having 1 or less carbon atoms
  • R u Is a functional group represented by the formula (1), a functional group represented by the formula (2), or a functional group represented by the formula (3).
  • R n is a functional group represented by the formula (3).
  • silver is an alkylene group having 1 to 3 carbon atoms
  • R n may be a functional group represented by the formula (1), a functional group represented by the formula (2), or a functional group represented by the formula (3).
  • examples of the first (meth) acrylate repeating unit represented by Formula 4 include a repeating unit derived from glycidyl methacrylate represented by the following Formula 4-1 or 3, 4-epoxycyclohexylmethylmethacrylate 4-2 derived from the formula (A) shown below in Synthesis Example 3, and the following Formula (4-4) derived from the formula (B) shown in the following Synthesis Example 4,
  • the photopolymerizable and thermosetting copolymers may contain a repeating unit of the (meth) acrylate system in which an organic functional group including an alkenyl group is bonded to the branched chain end.
  • the second (meth) acrylate repeating unit is contained in the second (meth) acrylate repeating unit, and the photocuring is performed by the light irradiation with the alkenyl group contained in the second (meth) acrylate repeating unit to form a dense cured structure have.
  • a chain formed through polymerization reaction of a double bond contained in (meth) acrylate is referred to as a main chain
  • a chain extending in a branch shape from the main chain is branched Or side chain (side chain).
  • the repeating unit of the (meth) acrylate is a repeating unit contained in the homopolymer of the (meth) acrylate monomer.
  • the repeating unit is a repeating unit derived from the polymerization of a vinyl group contained in the main chain (meth) ) ≪ / RTI > acrylate monomers. That is, in the second (meth) acrylate repeating unit, the branched chain terminal at which the organic functional group including an alkenyl group is bonded may mean the terminal of the ester functional group contained in the (meth) acrylate repeating unit.
  • the branch chain is an alkyl ester group (R 'COO- wherein R' is an alkyl group having 1 to 10 carbon atoms) substituted with a hydroxyl group and having 1 to 20 carbon atoms or a carbon number of 1 to 10, Or an oxyalkyl ester group having 1 to 20 carbon atoms substituted with a hydroxy group, or an alkyl ester group substituted with a hydroxy group-substituted C3-C30, or C3-C10 cycloalkyl group, 30, or a multi-ring alkyl ester group having 8 to 15 carbon atoms, or an alkyl ester group substituted with a hydroxyl group-substituted multi-ring alkyloxy group having 7 to 30 carbon atoms or 8 to 15 carbon atoms.
  • the organic functional group including the alkenyl group may be substituted at the terminal of the cycloalkyl group having 3 to 30 carbon atoms.
  • the alkenyl group may be bonded to the end of the multi-ring alkyl group having 7 to 30 carbon atoms and contained in the polycyclic alkyl ester group having 7 to 30 carbon atoms Containing organic functional groups may be substituted.
  • the terminal of the polycyclic alkyl group having 7 to 30 carbon atoms contained in the polycyclic alkyloxy group having 7 to 30 carbon atoms may be substituted.
  • the hydroxy group may be substituted with a branched alkyl group having 1 to 10 carbon atoms in the alkyl ester group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or a polycyclic alkyl having 10 to 30 carbon atoms May be substituted with 10 to 30 multibranched alkyl groups contained in the stator group or 10 to 30 multibranched alkyl groups included in the above multichannel alkyloxy groups having 10 to 30 carbon atoms.
  • the hydroxy group can be derived through the ring opening reaction of an epoxy group contained in the above-mentioned first (meth) acrylate repeating unit, more specifically, the epoxy group contained in the first (meth) acrylate repeating unit, And a compound containing an organic functional group including an alkenyl group ol.
  • the organic functional group including the alkenyl group may include both a functional group composed solely of an alkenyl group or a functional group having an alkenyl group bonded to another organic functional group.
  • a (meth) acryloyl group, a (meth) acryloyloxy And the like can be used, and a methacryloyloxy group can be preferably used.
  • the second (meth) acrylate repeating unit may be represented by the following general formula (5).
  • R 12 to R 14 are each independently any one of hydrogen and an alkyl group having 1 to 10 carbon atoms
  • L 2 is a direct bond or an alkylene group having 1 to 20 carbon atoms
  • L 3 represents an alkylene group having 1 to 20 carbon atoms substituted with a hydroxyl group or a cycloalkylene group having 3 to 30 carbon atoms substituted with a hydroxy group or a poly ring alkyl group having 7 to 30 carbon atoms substituted with a hydroxy group
  • R &lt 15 &gt
  • R 12 and R 14 are each independently hydrogen
  • R 13 is an alkyl group having 1 to 3 carbon atoms
  • L 2 is a direct bond or an alkylene group having 1 to 10 carbon atoms
  • L 3 is an alkylene group having 1 to 5 carbon atoms substituted with a hydroxy group, or a cycloalkylene group having 3 to 10 carbon atoms substituted with a hydroxy group, or a cycloalkylene group having a carbon number of 8 To 15 &lt
  • RTI ID 0.0 &gt
  • polycyclic < / RTI &gt
  • L 2 is a direct bond and L 3 is a polycyclic alkylene group having 10 to 20 carbon atoms substituted with a hydroxy group.
  • L 2 is a group having 1 to 10 carbon atoms, yet of an alkylene group, or a carbon number from 1 to '10 oxyalkylene groups
  • L 3 is of a carbon number of 1 within the five substituted with hydroxy alkylene group, or a hydroxyl group
  • examples of the repetitive units of the geranyl (meth) acrylate represented by the formula (5) include the following formulas (5-1) to (5-4) Terminal epoxy group may be prepared by reacting with (meth) acrylic acid.
  • the molar ratio between the repeating unit of the (meth) acrylate and the repeating unit of the second (meth) acrylate may be from 99: 1 to 1:99.
  • the photopolymerizable and thermosetting copolymers contain both the first (meth) acrylate repeating unit and the twelve (meth) acrylate repeating unit, so that the photocuring property and the low-temperature thermosetting property can be realized at the same time.
  • (Meth) acrylate repeating unit is preferably used in an amount of 10 to 90 moles, or 20 to 70 moles, or 30 to 50 moles, based on 100 moles of the first (meth) acrylate repeating unit . If the content of the second (meth) acrylate repeating unit is less than 10 moles per 100 moles of the above-mentioned (meth) acrylate repeating units, the residual copolymer may cause a residue problem.
  • R 16 to R 26 each independently represent hydrogen; Hydrogen; A halogen group; An alkyl group having 1 to 20 carbon atoms; An alkoxy group having 1 to 20 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; An alkenyl group having 2 to 20 carbon atoms; Or any one of a monocyclic or polycyclic cycloalkyl group having a carbon number of 3 to 30, and, L 4 is a bond or an alkylene group having 1 to 20 carbon atoms. And an oxyalkylene group having 1 to 20 carbon atoms.
  • R 16 and R 18 are hydrogen, R 17 is a methyl group, L 4 is a methylene group, Ri 9 may be a phenyl group. That is, the third (meth) acrylate repeating unit may be a repeating unit derived from benzyl methacrylate.
  • R 20 and R 21 may be hydrogen, and R 22 may be a phenyl group.
  • R 22 may be a phenyl group.
  • 3 ⁇ 4 3 , 3 ⁇ 4 4 and 5 may be hydrogen and R 26 may be a phenyl group. That is, the maleimide repeating unit represented by Chemical Formula 7 may be a repeating unit derived from N-phenylmaleimide, and the vinyl repeating unit represented by Chemical Formula 8 may be a styrene derived repeating unit.
  • (Meth) acrylate repeating unit and the first (meth) acrylate repeating unit is in the range of 1:99 to 99: 1, and the second (meth) acrylate repeating unit and the second ) Acrylate repeat units may be from 1:99 to 99: 1.
  • the first (meth) acrylate repeating unit, the second (meth) acrylate repeating unit, and the third (meth) acrylate repeating unit are used together, technical and chemical resistance Effects can be realized.
  • the weight average molecular weight (GPC measurement) of the photopolymerizable and thermosetting copolymers may be from 1,000 g / mol to 100,000 g / m.
  • the copolymer having photo-curable properties and thermosetting properties is a copolymer of a 1 (meth) acrylate repeating unit in which an organic functional group including an epoxy group is bonded to a branched chain terminal; A second (meth) acrylate repeating unit in which an organic functional group containing an alkenyl group is bonded to a branched chain terminal;
  • the copolymer having the photocurable property and the thermosetting property may not further contain additional repeating units other than the above-mentioned five repeating units. Accordingly, the copolymer having photo-curing property and thermosetting property can secure high reliability by suppressing spontaneous intracellular reaction before curing proceeds.
  • Examples of the method of synthesizing the copolymer having the photocurable property and the thermosetting property are not limited.
  • Examples of the (meth) acrylate monomer having an epoxy group-substituted organic functional group at the terminal thereof include glycidyl methacrylate or 3,4-epoxycyclohexylmethyl methacrylate, And the following formula 4-4 derived from the formula B of the following synthesis example 4, and the like.
  • Examples of the compound containing an organic functional group containing the alkenyl group include methacrylic acid, .
  • benzyl methacrylate, N-phenylmaleimide, and styrene may be added as other monomers used in the synthesis of co-polymers.
  • a photopolymerizable and thermosetting copolymer of this embodiment A photopolymerizable monomer having at least two photocurable unsaturated functional groups; And a photoinitiator may be provided.
  • the photopolymerizable monomer may be a compound having a photocurable unsaturated functional group such as, for example, two or more polyfunctional vinyl groups.
  • the photopolymerizable monomer may form a crosslinked structure with the unsaturated functional group of the copolymer having photocurable and thermosetting properties A cross-linking structure due to photo-curing can be formed during exposure.
  • the light-sensitive resin composition in the exposed portion can be left on the substrate without being subjected to alkali development.
  • Such a photopolymerizable monomer may be a liquid at room temperature, Accordingly, the viscosity of the phase-inversion photosensitive resin composition can be adjusted according to the application method, and the alkali developability of the non-visible portion can be further improved.
  • an acrylate compound having at least two photocurable unsaturated functional groups can be used.
  • Water-soluble acrylate compounds such as polyethylene glycol diacrylate, polypropylene glycol diacrylate, and polypropylene glycol diacrylate;
  • Polyfunctional polyester acrylate compounds of polyhydric alcohols such as trimethyl acrylate, propane triacrylate, pentaerythritol tetraacrylate, or dipentaerythritol hexaacrylate;
  • Acrylate compounds of polyfunctional alcohols such as trimethylol propane or hydrogenated bisphenol A or phenol oxidized adducts of polyhydric phenols such as bisphenol A and biphenol and / or propylene oxide adducts
  • Acrylate compounds modified with caprolactone, and photosensitive (meth) acrylate compounds such as a methacrylate compound which reacts with the above-mentioned acrylate compounds can be used, and these compounds can be used alone Or two or more of them may be used in combination.
  • a polyfunctional (meth) acrylate compound having at least two (meth) acryloyl groups in one molecule can be preferably used.
  • pentaerythritol can be used as triacrylate, trimethylol Propane triacrylate, dipentaerythritol hexaacrylate, or caprolactone modified ditrimethyl propane tetraacrylate can be suitably used.
  • examples of commercially available photopolymerizable monomers include DPEA-12 of Kayarad and the like.
  • the content of the photopolymerizable monomer may be 0.1 wt% to 30 wt%, or 1 wt% to 20 wt% based on the total weight of the photosensitive resin composition. If the content of the photopolymerizable monomer is too small, the photocuring may become insufficient. If the content of the photopolymerizable monomer is excessively large, the dryability of the cured film may deteriorate and the physical properties may be deteriorated.
  • the photoinitiator has a role of initiating radical photocuring between a photopolymerizable monomer and a copolymer having photo-curable properties and thermosetting properties, for example, in the exposed portion of the photosensitive resin composition.
  • benzoin such as benzoin, benzoin methyl ether, benzoin ethyl ether and the like, and alkyl ethers thereof; Acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 4- (1-t-butyldoxy-
  • Acetophenones such as 1-methylethyl) acetophenone;
  • Anthraquinones such as 2-methyl anthraquinone, 2-amyl anthraquinone, 2-t-butyl anthraquinone, and 1-chloro anthraquinone;
  • Thioxanthones such as 2, 4-dimethylthioxanthone, 2,4-diisopropylthioxanthone and 2-chlorothioxanthone;
  • Ketal such as acetophenone dimethyl ketal and benzyl dimethyl ketal;
  • Benzophenones such as benzophenone, 4- (l-butyldioxy-1-methylethyl) benzophenone, and 3,3'-benzophenone such as 4,4'-tetrakis (t-butyldioxycarbonyl) You can use the same materials. Further, 2-methyl-1- [4- (methylthio) phenyl]
  • TPO IRGACURE 819, manufactured by Ciba Specialty Chemicals, etc.
  • IRGACURE 819 manufactured by Ciba Specialty Chemicals, etc.
  • Examples of preferred photoinitiators include oxime esters.
  • Specific examples of the oxime ester include 2- (acetyloxyiminomethyl) thioxanthien-9-one, (1, 2-octanediyl, 1- [4- (phenylthio) phenyl] Benzoyloxime)), (ethanone, 1 [9-ethyl Yl] -, 1- (0-acetyloxime)), and the like.
  • Examples of commercially available products include GGI-325, Irugacure 0XE01, Irugacure 0XE02, ADEKA N-1919, and Chiron Specialty Chemicals Darocur TP0 from Chiba Specialty Chemicals.
  • the content of the photoinitiator is based on the total amount of resin composition 0.1 "increase% to
  • the content of the photoinitiator is too small, photocuring may not occur properly. On the contrary, if the content is excessively large, the resolution of the photosensitive resin composition may be lowered or the reliability of the patterned film may not be uniform.
  • the photosensitive resin composition includes a solvent; And at least one selected from the group consisting of fillers, pigments and additives.
  • the filler added in this way enhances thermal stability, dimensional stability by heat, and resin adhesion. It also acts as an extender pigment by enhancing the color.
  • inorganic or organic layer precursors can be used, for example, barium sulfate, barium titanate, amorphous silica, crystalline silica, fused silica, spherical silica, talc, clay, magnesium carbonate, calcium carbonate, aluminum oxide ), Aluminum hydroxide, mica, and the like.
  • the pigment exhibits visibility and hiding power, and as the pigment, red, blue, green, yellow, and a color pigment can be used.
  • Pigment Green 7, Pigment Gran 36, Solvent Green 3, Solvent Green 5, Solvent Green 20, Solvent Green 28, and the like can be used as green pigments.
  • Examples of the yellow pigments include anthraquinone pigments, isoindolinone pigments, condensed azo pigments, and benzimidazolone pigments.
  • pigments include Pigment Yellow 108, Pigment Yellow 147, Pigment Yellow 151, Pigment Yellow 166, Yellow 181, Pigment Yellow 193, and the like.
  • As the red pigment 254 pieces of Pigment Red can be used.
  • the content of the pigment is preferably 0.1 wt% to 10 wt%, or 0.5 wt% to 5 wt% with respect to the total weight of the resin composition.
  • the additive may be added in the role of removing bubbles of the resin composition or removing the popping or crater on the surface during the film coating, imparting flame retardancy, controlling the viscosity, and catalyst.
  • thickeners such as fine silica, organic bentonite, montmorillonite and the like; Defoaming agents and / or leveling agents such as silicones, fluorides, and polymers; Silane coupling agents such as imidazole, thiazole and triazole; Flame retardants such as phosphorus flame retardants and antimony flame retardants, and the like.
  • BYK-380N, BYK-307, BYK-378, and BYK-350 of BYK-Chemie GmbH can be used as the leveling agent in removing the surface popping or crater during film coating.
  • the content of the additive is preferably 0.01 wt% to 10 wt% with respect to the total weight of the resin composition.
  • the solvent may be used by dissolving the resin composition or by intensively using one or more solvents to give an appropriate viscosity.
  • the solvent examples include ketones such as methyl ethyl ketone and cyclohexanone; Aromatic hydrocarbons such as rubrene, xylene, and tetramethylbenzene; Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether; Glycol ethers (salosorb) such as propylene glycol monomethyl ether, propylene glycol monoethyl ether, dipropylene glycol diethyl ether and triethylene glycol monoethyl ether; Ethyl acetate, butyl acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol mono
  • the content of the solvent may be 5% by weight to 50% by weight based on the total weight of the resin composition. When the content is less than 5% by weight, the viscosity is high and the coating property is poor. When the content is more than 50% by weight, the drying is not performed well, and the stickiness is increased.
  • the photosensitive resin composition may further include an acid-denaturated or thermosetting binder, if necessary.
  • an acid-denaturated or thermosetting binder include various kinds of known various types of photosensitive resin compositions
  • the compounds, oligomers, or polymers can be applied without limitation. m. Photosensitive resin film
  • a copolymer having photo-curable and thermosetting properties of this embodiment and a cured product of a photopolymerizable monomer having two or more photocurable unsaturated functional groups, may be provided.
  • the photosensitive resin film may be a single film that does not include a pattern, or may include a pattern film including a pattern due to an exposure phenomenon.
  • the photosensitive resin film may be prepared by: 1) applying a photosensitive resin composition of another embodiment to a substrate to form a coating film; 2) drying the coating film; 3) irradiating the dried coating film with light to cure the coating; And 4) thermosetting the photocured film at 50 ° C to 250 ° C. '
  • the photosensitive resin composition includes all the contents of the other embodiments described above.
  • the method of applying the photosensitive resin composition to the substrate is not particularly limited, and for example, screen printing, offset printing, flexographic printing, ink jet, etc. can be used.
  • the photosensitive resin composition may be a copolymer having photo-curable properties and thermosetting properties according to the embodiment of the present invention; A photopolymerizable monomer having at least two photocurable unsaturated functional groups; And a photoinitiator dissolved or dispersed in an organic solvent have.
  • the step of drying the coating film (step 2) is for removing the solvent and the like used in the photosensitive resin composition.
  • heating of the coating film or evaporation of vacuum may be used.
  • the drying is performed at a temperature of preferably 50 ° C to 130 ° C, more preferably 70 ° C to 120 ° C.
  • the step (step 3) of irradiating light to the dried coating film by light irradiation is a step of irradiating light to the coating film dried in step 2 and curing the coating film.
  • the organic functional group containing the alkenyl group in the second (meth) acrylate repeating unit contained in the copolymer having photo-curable and thermosetting properties of the embodiment is cured by light irradiation Structure can be formed.
  • exposure is performed with a light beam (UV or the like) having a certain wavelength band.
  • the exposure may be selectively exposed with a photomask, or may be directly pattern-exposed with a laser direct exposure apparatus.
  • the amount of exposure depends on the thickness of the coating, but is preferably 0.1 mJ / cm 2 to 1,000 mJ / cuf.
  • a development step may be performed using an alkali solution or the like, if necessary.
  • the alkali solution may be an aqueous alkali solution such as potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium phosphate, sodium silicate, ammonia, amines and the like.
  • the step (step 4) of thermally curing the photocured coated film at 50 ° C to 250 ° C is a step of performing a low-temperature heat treatment on the photocured coating film in step 3.
  • the low-temperature heat treatment temperature is preferably 200 ° C or lower.
  • the low temperature heat treatment temperature is 50 ° C to 250 ° C, more preferably 70 ° C to 150 ° C, or 80 ° C to 120 ° C.
  • a heating means such as a hot plate, a hot air circulation path, an infrared ray furnace, or the like.
  • the organic functional group including the epoxy group in the first (meth) acrylate repeating unit included in the copolymer having photo-curable and thermosetting properties of the above-mentioned embodiment is thermally cured by heat treatment to form a cured structure .
  • the photosensitive resin film can be obtained by copolymerizing a photocurable and a curing-curable copolymer of the above-mentioned embodiment according to the photocuring and thermosetting;
  • the crosslinking structure in which the alkenyl group of the photopolymerizable and thermosetting copolymer and the unsaturated functional group of the photosensitizing monomer are cross-linked by photocuring.
  • the photosensitive resin film may further include a small amount of a photoinitiator remaining in the photo-curing state, or a pigment or additive added as needed, dispersed in the cured product.
  • the thickness of the photosensitive resin film is not particularly limited, but is freely adjustable within a range of 0.01 m to 1000, for example.
  • the thickness of the sense of polarization resin film is increased or decreased by a certain value can be changed as long as the physical properties, also a certain value, measured in the photosensitive resin film.
  • a color filter including the photosensitive resin film of the another embodiment may be provided.
  • the content of the photosensitive resin film may include all of the above-mentioned contents in the other embodiments.
  • the photosensitive resin film used for the color filter may contain the pigment dispersed in the cured product.
  • thermosetting resin composition having excellent thermosetting property at a relatively low temperature and capable of progressing light curing by light irradiation and having excellent durability, chemical resistance and storage stability through layered curing ,
  • a photosensitive resin composition using the same, a photosensitive resin film, a color filter, and a color filter may be provided.
  • the resin solution thus obtained was subjected to air polymerization at a temperature of 120 ° C for 16 hours while maintaining a temperature of not more than 50 ° C. and a post-decarboxylic acid content of 0.1 wt%.
  • the weight average molecular weight of the prepared photopolymerizable and thermosetting copolymers was 4,500 g / m 2, the content of the repeating unit of (meth) acrylate in which the branched chain terminal was replaced by the epoxide group was 49 mol%, the branched chain terminal
  • the (meth) acrylate repeating unit content substituted with an alkenyl group was 21 mol%.
  • Copolymers having photocurable properties and thermosetting properties were synthesized in the same manner as in Synthesis Example 1, except that 3, 4-epoxycyclohexylmethyl methacrylate was used instead of glycidyl methacrylate.
  • the prepared photo-curable and thermosetting copolymer had a weight average molecular weight of 4,700 g / mol, a content of (meth) acrylate repeating unit in which the branch chain terminal was substituted with an epoxy group, 49 mol / The content of (meth) acrylate repeating units whose terminals were substituted with alkenyl groups was 21 mol%.
  • a copolymer having photo-curable properties and thermosetting properties was synthesized in the same manner as in Synthesis Example 1, except that the compound represented by the following formula (A) was used instead of glycidyl methacrylate.
  • Copolymers having photocurable properties and thermosetting properties were synthesized in the same manner as in Synthesis Example 1, except that the compound represented by the following formula (B) was used instead of glycidyl methacrylate.
  • the temperature of the prepared resin solution was lowered to 90 ° C and 5.5 wt% of 1, 2,5,6-tetrahydrophthalic anhydride was added in an air atmosphere for 24 hours.
  • the prepared resin had a weight average molecular weight of 8, 100 g / m and an acid value of 83 KOH mg / g.
  • the content of the (meth) acrylate repeating unit in which the branched chain terminal was substituted with an epoxy group was 0 and the branched chain terminal was an alkenyl group
  • the substituted (meth) acrylate repeating unit content was 40 mol%.
  • the photosensitive resin composition was coated on a 5 cm x 5 cm glass at 230 rpm and prebaked at 100 ° C for 100 seconds. Thereafter, the resist film was exposed to 40 mJ / cm 2 of energy, developed, and post-baked at 100 ° C for 30 minutes to prepare a photosensitive resin pattern film.
  • thermosetting resin represented by the following formula (C) was used instead of the copolymer having photo-curing property and thermosetting property obtained in Synthesis Example 1
  • a photosensitive resin composition and a photosensitive resin pattern film were prepared in the same manner as in Example 1, except that BPN-110 (Kukdo Chemical Co., Ltd.) was used.
  • a photosensitive resin composition and a photosensitive resin composition were prepared in the same manner as in Example 2, except that the thermosetting resin used in Comparative Example 1 was used instead of the copolymer having photo-curable property and thermosetting property obtained in Synthesis Example 1, Thereby preparing a photosensitive resin pattern film.
  • Comparative Example 3
  • a photosensitive resin composition and a photosensitive resin composition were prepared in the same manner as in Example 3, except that the thermosetting resin used in Comparative Example 1 was used instead of the copolymer having photocurable property and thermosetting property obtained in Synthesis Example 1, Thereby preparing a photosensitive resin pattern film. Compare
  • a photosensitive resin composition was prepared in the same manner as in Example 1, except that the copolymer resin obtained in Comparative Synthesis Example 1 was used instead of the copolymer having photo-curable property and thermosetting property obtained in Synthesis Example 1, To prepare a composition and a photosensitive resin pattern film. Compare 15
  • a photosensitive resin composition and a photosensitive resin composition were prepared in the same manner as in Example 2, except that the copolymer resin obtained in Comparative Synthesis Example 1 was used instead of the copolymer having photo-curable and thermosetting properties obtained in Synthesis Example 1, To prepare a resin pattern film.
  • a photosensitive resin composition and a photosensitive resin composition were prepared in the same manner as in Example 3, except that the copolymer resin obtained in Comparative Synthesis Example 1 was used instead of the copolymer having photo-curable and thermosetting properties obtained in Synthesis Example 1, To prepare a resin pattern film.
  • Example 3 A photosensitive resin composition and a photosensitive resin composition were prepared in the same manner as in Example 3, except that the copolymer resin obtained in Comparative Synthesis Example 1 was used instead of the copolymer having photo-curable and thermosetting properties obtained in Synthesis Example 1, To prepare a resin pattern film.
  • a photosensitive resin composition containing a pigment having a color different from that of the pigment included in the light-sensitive resin pattern film was coated / developed on the photosensitive resin pattern film obtained in the above Examples and Comparative Examples, and then the photosensitive resin pattern film
  • the color change was measured as MPCD (Minimum Perceptable Color Dielectric), and pattern shift and swelling were observed using optical equipment.
  • the pigment elution was judged according to the following criteria, Table 1 shows the results.
  • the photosensitive resin pattern film After coating / exposing / curing an overcoat photosensitive liquid on the photosensitive resin pattern film obtained in the above-mentioned Examples and Comparative Examples, the photosensitive resin pattern film was subjected to color evaluation as MPCD (Minimum Perceptable Color Dielectric) The pattern was shifted and swelling was observed using an optical instrument. The pigment elution was judged according to the following criteria, and the results are shown in Table 1 below.
  • MPCD Minimum Perceptable Color Dielectric
  • the photosensitive resin compositions obtained in the above Examples and Comparative Examples were measured for development time and the development time (second) after standing at room temperature for 2 weeks, and the results are shown in Table 1 below. The smaller the change in the development time after the production day and 2 weeks, the better the storage stability.

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Abstract

La présente invention concerne un copolymère ayant des propriétés photodurcissables et thermodurcissables, qui présente un excellent durcissement à la chaleur à des températures relativement basses et peut également subir un processus de photodurcissement lors de l'exposition à la lumière, ce qui garantit une excellente durabilité, une excellente résistance chimique et une excellente stabilité au stockage grâce à un durcissement suffisant. L'invention concerne également une composition de résine photosensible, un film de résine photosensible, et un filtre coloré l'utilisant.
PCT/KR2018/013652 2017-11-10 2018-11-09 Copolymère ayant une propriété photodurcissable et thermodurcissable, et composition de résine photosensible, film de résine photosensible, et filtre coloré l'utilisant Ceased WO2019093827A1 (fr)

Priority Applications (2)

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JP2019553075A JP6911272B2 (ja) 2017-11-10 2018-11-09 感光性樹脂組成物、感光性樹脂フィルム、およびカラーフィルタ
CN201880032826.2A CN110709435B (zh) 2017-11-10 2018-11-09 可光固化且可热固化共聚物以及使用其的光敏树脂组合物、光敏树脂膜和滤色器

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KR1020180136598A KR102118627B1 (ko) 2017-11-10 2018-11-08 광경화성 및 열경화성을 갖는 공중합체, 이를 이용한 감광성 수지 조성물, 감광성 수지 필름, 및 컬러필터

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KR20020066504A (ko) * 2001-02-12 2002-08-19 주식회사 엘지화학 패턴 스페이서용 감광성 수지 조성물
KR20090081208A (ko) * 2008-01-23 2009-07-28 주식회사 엘지화학 바인더 수지 및 이를 포함하는 감광성 수지조성물과, 이감광성 수지조성물에 의해 제조된 컬럼스페이서
KR20100016506A (ko) * 2007-05-11 2010-02-12 다이셀 가가꾸 고교 가부시끼가이샤 광 및/또는 열 경화성 공중합체, 경화성 수지 조성물 및 경화물
KR20120000278A (ko) * 2010-06-25 2012-01-02 주식회사 엘지화학 알칼리 가용성 바인더 수지 및 이를 포함하는 감광성 수지 조성물
KR101564872B1 (ko) * 2015-02-10 2015-10-30 동우 화인켐 주식회사 네가티브형 감광성 수지 조성물

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KR20020066504A (ko) * 2001-02-12 2002-08-19 주식회사 엘지화학 패턴 스페이서용 감광성 수지 조성물
KR20100016506A (ko) * 2007-05-11 2010-02-12 다이셀 가가꾸 고교 가부시끼가이샤 광 및/또는 열 경화성 공중합체, 경화성 수지 조성물 및 경화물
KR20090081208A (ko) * 2008-01-23 2009-07-28 주식회사 엘지화학 바인더 수지 및 이를 포함하는 감광성 수지조성물과, 이감광성 수지조성물에 의해 제조된 컬럼스페이서
KR20120000278A (ko) * 2010-06-25 2012-01-02 주식회사 엘지화학 알칼리 가용성 바인더 수지 및 이를 포함하는 감광성 수지 조성물
KR101564872B1 (ko) * 2015-02-10 2015-10-30 동우 화인켐 주식회사 네가티브형 감광성 수지 조성물

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