[go: up one dir, main page]

WO2024237536A1 - Composition photopolymérisable et dispositif électronique - Google Patents

Composition photopolymérisable et dispositif électronique Download PDF

Info

Publication number
WO2024237536A1
WO2024237536A1 PCT/KR2024/006061 KR2024006061W WO2024237536A1 WO 2024237536 A1 WO2024237536 A1 WO 2024237536A1 KR 2024006061 W KR2024006061 W KR 2024006061W WO 2024237536 A1 WO2024237536 A1 WO 2024237536A1
Authority
WO
WIPO (PCT)
Prior art keywords
monomer
photopolymerizable composition
acrylate
chemical formula
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/KR2024/006061
Other languages
English (en)
Korean (ko)
Inventor
조성민
윤혁민
여태훈
이상훈
박종혁
이상민
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dongjin Semichem Co Ltd
Original Assignee
Dongjin Semichem Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020240059023A external-priority patent/KR20240166923A/ko
Application filed by Dongjin Semichem Co Ltd filed Critical Dongjin Semichem Co Ltd
Priority to CN202480027797.6A priority Critical patent/CN121013872A/zh
Publication of WO2024237536A1 publication Critical patent/WO2024237536A1/fr
Anticipated expiration legal-status Critical
Pending legal-status Critical Current

Links

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
    • 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
    • C08F220/10—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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics

Definitions

  • the present invention relates to a photopolymerizable composition, and more particularly, to a photopolymerizable composition, an optical member, and an electronic device.
  • the brightness increase rate changes depending on the refractive index of the resin forming the prism structure.
  • the brightness increase rate increases as the refractive index of the resin forming the prism increases. Therefore, with regard to the light-transmitting optical film, research and development is being conducted in the direction of increasing the refractive index of the resin forming the prism structure.
  • An object of the present invention is to provide a photopolymerizable composition that improves inkjet ejection characteristics.
  • Another object of the present invention is to provide a photopolymerizable composition that increases the refractive index and transmittance of an optical member and reduces haze.
  • Another object of the present invention is to provide an optical member cured with the photopolymerizable composition.
  • Another object of the present invention is to provide an electronic device including the optical member.
  • a photopolymerizable composition comprising: a first monomer having a first photocurable functional group; a second monomer having a second photocurable functional group; and an initiator; wherein the first and second monomers satisfy the following formula 1.
  • C is the absolute value of the deviation of the surface tension of the second monomer with respect to the surface tension of the first monomer (mN/m)
  • A is the surface tension of the first monomer (mN/m) at 25°C
  • B is the surface tension of the second monomer (mN/m) at 25°C.
  • the liquid phase refractive index of the first monomer in the first aspect may be 1.57 or more.
  • the surface tension of the first monomer in the first or second aspect may be 41 mN/m or less.
  • the first monomer may include an aromatic compound including one or more aromatic ring structures or one or more heteroatoms.
  • the first monomer may include a structure represented by the following chemical formula 1.
  • A includes at least one structure of a substituted or unsubstituted aryl group; a substituted or unsubstituted aromatic heterocycle; and a substituted or unsubstituted bicyclic;
  • X 1 is a direct bond, or a divalent linking group having 1 to 20 carbon atoms with or without one or more oxygen atoms
  • X 2 is a direct bond, or a divalent linking group having 1 to 20 carbon atoms with or without one or more oxygen atoms
  • R is the first photocurable functional group.
  • the substituted or unsubstituted bicyclic may be a bridged bicyclic structure.
  • the bivalent linking group in X 1 and X 2 that does not include an oxygen atom may include at least one or more of an alkylene group, an alkenylene group, and an alkynylene group.
  • the first monomer may include at least one compound selected from the group consisting of benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxybenzyl (meth)acrylate, O-phenyl phenoxyethyl (meth)acrylate, biphenyl (meth)acrylate, biphenyl ethyl (meth)acrylate, and compounds represented by the following chemical formulas 2 to 9.
  • each R is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
  • each n is independently an integer from 0 to 10.
  • each n can be independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • the purity of the first monomer may be 95% or higher.
  • the purity of the first monomer may be 98% or more.
  • the content of the first monomer may be 30 to 90 parts by weight based on 100 parts by weight of the total monomer including the first monomer and the second monomer.
  • the second monomer may include a structure represented by the following chemical formula 10.
  • B and B ⁇ include the second photocurable functional group which is the same as or different from each other
  • Y includes a substituted or unsubstituted hydrocarbon structure having 4 to 50 carbon atoms, which may or may not include one or more oxygen atoms
  • Y may include, for example, a divalent linking group in which all atoms linked to the second photocurable functional group are oxygen atoms, and may be specifically -O-(CH 2 )xO-.
  • x may be 1 or more, and may be specifically 1, 2, 3, 4, 5, 6, 7, 8, or 9.
  • Y is an aliphatic or aromatic structure having 4 to 50 carbon atoms, and may include an alkylene oxide having 6 or more carbon atoms, an alkylene group having 6 or more carbon atoms, or an alkenylene group having 6 or more carbon atoms.
  • the second monomer may include at least one selected from the group consisting of ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, butanediol dimeth)acrylate, pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, isostearyl acrylate, lauryl acrylate, 1,6-hexanediol ethoxylate di(meth)acrylate, and a compound represented by the following chemical formula 11.
  • the alkyl group may be a straight-chain or branched alkyl group having 1 to 5 carbon atoms.
  • b may be 0 and a and c may be integers from 1 to 20.
  • the content of the initiator may be 0.5 to 10 parts by weight based on 100 parts by weight of the total monomer including the first monomer and the second monomer.
  • the initiator may include a radical initiator.
  • a photopolymerizable composition can be provided, further comprising at least one selected from the group consisting of a surfactant, an amine enhancer, and a photosensitizer in any one of the first to sixteenth aspects.
  • the content of the surfactant may be 0.001 to 20 parts by weight based on 100 parts by weight of the total monomer including the first monomer and the second monomer.
  • a photopolymerizable composition in a solvent-free form according to any one of the first to eighteenth aspects can be provided.
  • a photopolymerizable composition having an absolute viscosity of 5 to 40 cP measured at 25° C. in any one of the first to 19th aspects can be provided.
  • an optical member including a cured film cured by the photopolymerizable composition according to any one of the first to twentieth aspects can be provided.
  • the haze of the cured film may be 3% or less and the average transmittance within a wavelength of 380 to 720 nm may be 95% or more.
  • an electronic device including an optical member according to the 21st or 22nd aspect is provided.
  • the viscosity and surface tension of a photopolymerizable composition are controlled to an appropriate level, so that the ejection characteristics of ink from a nozzle of an inkjet head can be improved.
  • the photopolymerizable composition can improve optical properties by increasing the refractive index and light transmittance of a cured optical member and lowering the haze value.
  • Figure 1 shows the results of inkjet ejection characteristics for photopolymerizable compositions according to examples and comparative examples.
  • Figure 2 shows inkjet droplet parameter results for photopolymerizable compositions according to examples and comparative examples.
  • At least one of a, b and c may include a, b or c alone, or a combination of two or more selected from the group consisting of a, b and c.
  • each embodiment may be combined unless there is a special description to the contrary.
  • the effect of the present invention may be defined as including the effect resulting from each embodiment and the effect occurring when each embodiment is organically combined.
  • Embodiments 1 and 2 may be organically combined with each other unless the context clearly indicates otherwise, and the effect of the present invention may include the effect occurring when Embodiments 1 and 2 are combined.
  • the numerical range indicated by the term "to" in this specification represents a numerical range that includes the values described before and after the term as the lower limit and the upper limit, respectively.
  • the numerical range disclosed in this specification can be understood as any numerical range that uses any one of the multiple lower limit values and any one of the multiple upper limit values as the lower limit and the upper limit, respectively.
  • a to b, or c to d are described in the specification, it can be understood that a or more and b or less, a or more and d or less, c or more and d or less, or c or more and b or less are described.
  • the term “layer” or film may include cases where the layer or film is formed not only over the entire region when observing the region where the layer or film exists, but also over a portion of the region.
  • the surface of the layer or film may be defined as including a flat shape, a non-flat shape, and a combination thereof; or a continuous shape, a discontinuous shape, and a combination thereof.
  • the coverage of the other member over the surface of the one member may be defined as 1% or more, 5% or more, 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, 80% or more, 85% or more, 90% or more, 95% or more, or 99% or more.
  • a plurality of particles form a clustered structure, it may be defined as a “layer or “film.”
  • the “weight average molecular weight” or “number average molecular weight” refers to a standard polystyrene-converted molecular weight, which can be analyzed using a GPC (gel permeation chromatography) device.
  • the developing solvent may be tetrahydrofuran (THF)
  • the column may be PL Olexis of Polymer Laboratories
  • the sample concentration may be 5 mg/mL
  • the sample injection amount may be 100 ⁇ l
  • the flow rate may be 1 mL/min
  • the detector may be Agilent High Temperature RI detector
  • the column temperature may be set to 40°C.
  • substituted means a group in which at least one hydrogen atom is substituted with a halogen atom, a hydroxyl group, a carboxyl group, a nitro group, an amine group, a sulfide group, a thiol group, an alkoxy group, an acetoxy group, a nitrile group, an aldehyde group, an ether group, an ester group, an acetal group, a ketone group, a C 1 to C 30 alkyl group, a C 2 to C 30 alkenyl group, a C 2 to C 30 alkynyl group, a C 1 to C 40 alkylsilyl group, a C 5 to C 40 arylsilyl group, a C 3 to C 30 cycloalkyl group, a C 3 to C 30 allyl group, a C 6 to C 30 aryl group, a heterocyclic group (e.g.
  • fused ring means a ring in which two or more rings are joined by sharing two or more atoms, and may include, for example, a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.
  • spiro structure means a structure having a spiro union, which means a connection formed by two rings sharing only one atom.
  • meth(acrylate) may be defined as containing an acrylate or methacrylate group.
  • a photopolymerizable composition comprising: a first monomer having a first photocurable functional group; a second monomer having a second photocurable functional group; and an initiator; wherein the first and second monomers satisfy the following formula 1.
  • C is the absolute value (mN/m) of the deviation of the surface tension of the second monomer with respect to the surface tension of the first monomer
  • A is the surface tension (mN/m) of the first monomer at 25°C
  • B is the surface tension (mN/m) of the second monomer at 25°C.
  • the viscosity and surface tension of the photopolymerizable composition are controlled to an appropriate level, so that ink can be well ejected from the nozzle of the inkjet head without clogging.
  • an optical member having a high refractive index, a low haze value, and high light transmittance can be implemented.
  • a photopolymerizable composition according to the present invention comprises a first monomer having a first photocurable functional group capable of increasing the refractive index of an optical member.
  • the first photocurable functional group may include a reactive functional group capable of photopolymerization in the presence of an initiator.
  • the first photocurable functional group may include any one selected from the group consisting of a (meth)acryl group, a carbon-carbon unsaturated bond, and a combination thereof.
  • the carbon-carbon unsaturated bond may be a carbon-carbon double bond or a carbon-carbon triple bond.
  • at least one carbon-carbon unsaturated bond may be included in the first monomer.
  • the (meth)acryl group may be an unsaturated carbonyl group including a carbon-carbon double bond composed of alpha and beta carbons; or a group in which a hydrogen atom or an alkyl group having 1 or more carbon atoms is bonded to the alpha carbon [alkyl (meth)acryl group].
  • the liquid refractive index of the first monomer may be 1.57 or higher, specifically 1.57 to 1.65, and more specifically 1.58 to 1.63.
  • the refractive index of the cured film by ultraviolet irradiation or the like can be increased.
  • the surface tension of the first monomer may be 43 mN/m or less, 42.4 mN/m or less, 41 mN/m or less, 40 mN/m or less, 39 mN/m or less, 38.9 N/m or less, 38 mN/m or less, or 37.8 mN/m or less, and specifically may be 37 mN/m or more and less than or equal to any one of the plurality of numerical values.
  • the surface tension of the first monomer when the surface tension of the first monomer satisfies the numerical range, the effect of improving the discharge characteristics when the photopolymerizable composition is used as ink in an inkjet printer can be further implemented, and the discharged photopolymerizable composition can be sufficiently cured.
  • the surface tension of the first monomer can be measured at 25°C using a surface tension meter (equipment name: K20 from KRUSS) by the Du Nouy Ring or Wilhelmy Plate method.
  • the first monomer may include an aromatic compound having at least one aromatic ring structure or at least one heteroatom.
  • the first monomer may include an aromatic compound having at least one aromatic ring structure or at least one heteroatom, thereby improving the optical properties of the optical member and at the same time controlling the surface tension and viscosity of the photopolymerizable composition to an appropriate level, thereby further improving the ejection properties of the ink.
  • the first monomer may include a structure represented by the following chemical formula 1.
  • A comprises at least one structure of a substituted or unsubstituted aryl group; a substituted or unsubstituted aromatic heterocycle; and a substituted or unsubstituted bridged bicyclic;
  • X 1 is a direct bond, or a divalent linking group having 1 to 20 carbon atoms with or without one or more oxygen atoms
  • X 2 is a direct bond, or a divalent linking group having 1 to 20 carbon atoms with or without one or more oxygen atoms
  • R is the first photocurable functional group.
  • the aryl group may include 1 or more, 2 or more, or 3 or more benzene rings.
  • the benzene ring may be a substituted or unsubstituted benzene ring.
  • the aromatic heterocycle may be an aromatic ring including 1 or more heteroatoms, and specifically, may be an aromatic ring including any one selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, and combinations thereof.
  • the bridged cyclic structure may have two rings sharing two carbon atoms, and any one or more hydrogen atoms bonded to the parent group of the bridged cyclic structure may be substituted with a functional group including a carboxyl group or the like.
  • the bridged ring structure may comprise a fused aromatic ring, specifically a naphthalene group, an anthracene group, a phenanthrene group, a perylene group, or a tetracene group.
  • the divalent linking group having 1 to 20 carbon atoms and containing at least one oxygen atom may include at least one of an ester group (-COO- or -OOC-), an ether group (-O-), and a ketone group (-CO-).
  • the divalent linking group may include at least one of an aliphatic structure and an aromatic structure having 1 to 20 carbon atoms. More specifically, the aliphatic structure may include at least one selected from the group consisting of an aliphatic chain structure, an aliphatic ring structure, and a combination thereof that satisfy the above-described carbon number range.
  • the aromatic structure may include at least one selected from the group consisting of an aryl group, a heteroaryl group, and a combination thereof that satisfy the above-described carbon number range.
  • the divalent linking group having 1 to 20 carbon atoms and containing at least one oxygen atom in the X 2 may include at least one of an ester group (-COO- or -OOC-), an ether group (-O-), and a ketone group (-CO-).
  • the divalent linking group may include at least one of an aliphatic structure and an aromatic structure having 1 to 20 carbon atoms. More specifically, the aliphatic structure may include at least one selected from the group consisting of an aliphatic chain structure, an aliphatic ring structure, and a combination thereof that satisfy the above-described carbon number range.
  • the aromatic structure may include at least one selected from the group consisting of an aryl group, a heteroaryl group, and a combination thereof that satisfy the above-described carbon number range.
  • A is a substituted or unsubstituted aryl group having 6 to 14 carbon atoms
  • X 1 is a direct bond
  • X 2 may be a divalent linking group having 1 to 10 carbon atoms that may or may not contain one or more oxygen atoms, and specifically, may be a divalent linking group having 1 to 10 carbon atoms that contains one or more oxygen atoms.
  • the optical properties of the optical member e.g., high refractive index and low haze
  • the surface tension and viscosity of the photopolymerizable composition are controlled to appropriate levels, thereby further improving the inkjet ejection properties.
  • the first monomer may include at least one compound selected from the group consisting of benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxybenzyl (meth)acrylate, O-phenyl phenoxyethyl (meth)acrylate, biphenyl (meth)acrylate, biphenyl ethyl (meth)acrylate, and compounds represented by the following chemical formulas 2 to 9.
  • the compound represented by the above chemical formula 2 may include at least one selected from the group represented by the above chemical formulas 2-1 and 2-2.
  • the compound represented by the above chemical formula 3 may include at least one selected from the group represented by the above chemical formulas 3-1 to 3-3.
  • the compound represented by the above chemical formula 4 may include at least one selected from the group represented by the above chemical formulas 4-1 to 4-3.
  • the compound represented by the above chemical formula 5 may include at least one selected from the group represented by the above chemical formulas 5-1 to 5-2.
  • the compound represented by the above chemical formula 6 may include at least one selected from the group represented by the above chemical formulas 6-1 to 6-6.
  • each R is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
  • each n is independently an integer from 0 to 10.
  • each n can be independently 0. 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • the purity of the first monomer may be 94% or more, 95% or more, 96% or more, specifically 98% or more, and more specifically 98.01% to 99.99%.
  • the inkjet ejection characteristics and the inkjet droplet parameter characteristics can be further improved. More specifically, even if the purity of the first monomer satisfies the range, when the absolute value (mN/m) of the deviation of the surface tension of the second monomer with respect to the surface tension of the first monomer exceeds 8.0 mN/m, a problem may occur in which the ejection characteristics of the photopolymerizable composition are not sufficiently improved.
  • the purity of the first monomer can be measured using liquid chromatography or gas chromatography.
  • the content of the first monomer may be 30 to 90 parts by weight, 40 to 80 parts by weight, 45 to 70 parts by weight, 50 to 60 parts by weight, or 55 to 65 parts by weight, based on 100 parts by weight of the total monomers including the first monomer and the second monomer.
  • the optical properties e.g., high refractive index and low haze
  • the surface tension and viscosity of the photopolymerizable composition are controlled to an appropriate level, thereby further improving the inkjet ejection characteristics.
  • the photopolymerizable composition according to the present invention comprises a second monomer having a second photocurable functional group to lower the viscosity of the photopolymerizable composition and control the curing speed and degree of the photopolymerizable composition.
  • the second photocurable functional group may be the same as or different from the first photocurable functional group described above.
  • the second monomer may include a structure represented by the following chemical formula 10, and more specifically, may include a compound represented by the following chemical formula 10.
  • B and B ⁇ include the second photocurable functional group which is the same as or different from each other
  • Y includes a substituted or unsubstituted hydrocarbon structure having 4 to 50 carbon atoms, which may or may not include one or more oxygen atoms
  • Y in the chemical formula 10 includes a substituted or unsubstituted hydrocarbon structure having 4 to 50 carbon atoms and containing one or more oxygen atoms
  • the Y may be a divalent linking group (-O-Rm- or -Rm-O-) containing oxygen atoms at one terminal (-O-Rm-O-) or both terminals.
  • Rm may be a straight-chain or branched alkylene group having 4 to 50 carbon atoms and containing or not containing one or more ether groups.
  • Y is an aliphatic or aromatic structure having 4 to 50 carbon atoms, and may include an alkylene oxide having 6 or more carbon atoms, an alkylene group having 6 or more carbon atoms, or an alkenylene group having 6 or more carbon atoms.
  • the second monomer since the second monomer includes a structure represented by the chemical formula 10, the absolute value (mN/m) of the deviation of the surface tension of the second monomer with respect to the surface tension of the first monomer may satisfy 8.0 mN/m or less.
  • the viscosity and surface tension of the photopolymerizable composition are controlled to an appropriate level, so that the ink can be well ejected from the nozzle of the inkjet head.
  • an optical member having a high refractive index, a low haze value, and high light transmittance can be implemented.
  • the second monomer may include at least one selected from the group consisting of ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, butanediol dimeth)acrylate, pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, isostearyl acrylate, lauryl acrylate, 1,6-hexanediol ethoxylate di(meth)acrylate, and a compound represented by the following chemical formula 11.
  • the alkyl group can be a straight-chain or branched alkyl group having 1 to 5 carbon atoms.
  • the content of the second monomer may be 10 to 70 parts by weight, 20 to 60 parts by weight, 30 to 55 parts by weight, or 40 to 50 parts by weight, based on 100 parts by weight of the total monomers including the first monomer and the second monomer.
  • the viscosity and surface tension of the photopolymerizable composition are controlled to an appropriate level, so that when the photopolymerizable composition is applied as an ink for inkjet printing, the discharge characteristics can be excellent.
  • the surface tension of the second monomer measured at 25° C. may be 30 mN/m or more, specifically 31 to 40 mN/m, and more specifically 32.8 to 39.3 mN/m.
  • the surface tension of the second monomer satisfies the numerical range, the viscosity and surface tension of the photopolymerizable composition are controlled to an appropriate level, so that the discharge characteristics can be excellent when the photopolymerizable composition is applied as an ink for inkjet printing.
  • a photopolymerizable composition comprising: a first monomer having a first photocurable functional group; a second monomer having a second photocurable functional group; and an initiator; wherein the first and second monomers satisfy the following formula 1.
  • C is the absolute value (mN/m) of the deviation of the surface tension of the second monomer with respect to the surface tension of the first monomer
  • A is the surface tension (mN/m) of the first monomer at 25°C
  • B is the surface tension (mN/m) of the second monomer at 25°C.
  • an optical member having a high refractive index, a low haze value, and high light transmittance can be implemented.
  • C can satisfy 5.0 mN/m or less, or 2.5 mN/m or less. According to one embodiment of the present invention, by satisfying C in the above formula 1, the viscosity and surface tension of the photopolymerizable composition are controlled, so that the ejection characteristics of ink from the nozzle of the inkjet head can be further improved.
  • the photopolymerizable composition according to the present invention comprises an initiator to initiate and promote the photocuring reaction of the first monomer and the second monomer described above.
  • the content of the initiator according to the present invention may be 0.5 to 10 parts by weight, 2 to 10 parts by weight, 3 to 9 parts by weight, 4 to 8 parts by weight, or 5 to 7 parts by weight, based on 100 parts by weight of the total monomers including the first monomer and the second monomer.
  • the photocuring reaction can sufficiently proceed and at the same time, the transmittance of the cured film in which the photopolymerizable composition is cured can be sufficiently increased.
  • the initiator may include a radical initiator that induces a photopolymerization reaction by a radical mechanism.
  • the weight ratio of the initiator and the first monomer may be 1:5 to 1:120. Specifically, when the weight ratio of the initiator and the first monomer (initiator: first monomer) satisfies the numerical range, the photocuring reaction may sufficiently proceed and at the same time, the transmittance of the cured film of the photopolymerizable composition may sufficiently increase.
  • the weight ratio of the initiator and the second monomer may be 1:3 to 1:90. Specifically, when the weight ratio of the initiator and the second monomer (initiator: second monomer) satisfies the numerical range, the photocuring reaction may sufficiently proceed and the transmittance of the cured film of the photopolymerizable composition may sufficiently increase.
  • the initiator is selected from the group consisting of 2,4-bistrichloromethyl-6-p-methoxystyryl-s-triazine, 2-p-methoxystyryl-4,6-bistrichloromethyl-s-triazine, 2,4-trichloromethyl-6-triazine, 2,4,-trichloromethyl-4-methylnaphthyl-6-triazine, 2-(o-chlorophenyl)-4,5-diphenyl imidazole dimer, 2-(o-chlorophenyl)-4,5-di(m-methoxyphenyl) imidazole dimer, 2-(o-fluorophenyl)-4,5-diphenyl imidazole dimer, 2-(-o-methoxyphenyl)-4,5-diphenyl imidazole dimer, 2,4,-di(p-methoxy phenyl)-5-phenyl imidazole dimer, 2-(2,4-dime
  • the photopolymerizable composition according to the present invention may further include at least one selected from the group consisting of a surfactant, an amine enhancer, and a photosensitizer, and specifically may include a surfactant.
  • the surfactant according to the present invention can improve the uniformity of the thickness and surface smoothness of a cured film of a photopolymerizable composition.
  • nonionic surfactants such as polyethylene oxyalkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and polyoxyethylene oleyl ether, polyoxyethylene aryl ethers such as polyethylene octyl phenyl ether and polyoxyethylene nonyl phenyl ether, and polyoxyethylene dialkyl esters such as polyethylene dilaurate and polyoxyethylene distearate; organosiloxane polymer KP341 (Shin-Etsu Chemical Co., Ltd.), (meth)acrylic acid copolymers such as No. 57 and 95 (Kyoeisha Yuyu Kagaku Kogyo Co., Ltd.), etc.
  • organosiloxane polymer KP341 Shin-Etsu Chemical Co., Ltd.
  • (meth)acrylic acid copolymers such as No. 57 and 95 (Kyoeisha Yuyu Kagaku Kogyo Co
  • the amine enhancer according to the present invention can increase the surface hardening degree of a cured film and at the same time reduce the haze of an optical member.
  • the amine group of the amine enhancer can capture oxygen radicals in the air and promote the reaction of an initiator.
  • the amine enhancer has a photocurable functional group, it can also form a crosslinking bond with the first and second monomers described above.
  • the amine enhancer is not particularly limited, and specifically can be ethyl dimethylamino benzoate, butoxyethyl dimethylamino benzoate, diethylaminoethyl (meth)acrylate, etc.
  • the photosensitizer according to the present invention can promote a photopolymerization reaction.
  • the photosensitizer can include at least one selected from the group consisting of isopropyl thioxanthone, pyrene, perylene, triphenylene, anthracene, 9,10-dibutoxyanthracene, 9,10-diethoxyanthracene, 3,7-dimethoxyanthracene, and 9,10-dipropyloxyanthracene.
  • the photopolymerizable composition may be a solventless form that does not contain a solvent.
  • the photopolymerizable composition may have an absolute viscosity of 5 to 40 cP measured at 25°C.
  • the absolute viscosity of the photopolymerizable composition satisfies the numerical range, the inkjet discharge characteristics may be improved.
  • the absolute viscosity of the photopolymerizable composition may be measured at 25°C using a viscometer (equipment name: BrookField Viscometer).
  • the inkjet droplet parameter (IDP) of the photopolymerizable composition satisfies the above numerical range, ink can be ejected well from the inkjet head without ink clogging.
  • the inkjet droplet parameter of the photopolymerizable composition may be a factor affecting at least one of the refractive index, haze value, and light transmittance of the cured film.
  • the photopolymerizable composition can provide an optical member including a cured film.
  • the cured film can have a haze of 3% or less, 2% or less, or less than 1.0%, and an average transmittance within a wavelength of 380 to 720 nm of 95% or more, 96% or more, or 97% or more.
  • the optical member may be an optical film or a patterned pattern film.
  • the cured film may be disposed on a substrate.
  • the substrate may be a silicon wafer or the like.
  • the optical member can be manufactured by applying the photopolymerizable composition of one embodiment described above onto the substrate using a Mayer bar, a coating applicator, an inkjet device, etc., and performing photocuring by exposing using an LED lamp or a metal halide lamp, etc.
  • the photopolymerizable composition can be applied in the form of a single film and then photocured to form an optical member in the form of a general optical film, but can also be applied in a certain pattern shape using the inkjet device and then photocured, if necessary.
  • the optical member can be in the form of a pattern film in which a cured film patterned in a polyhedral shape such as a prism structure is formed on the substrate.
  • the optical member such as the optical film or pattern film described above, may have a general thickness depending on its type or the structure of the electronic device to which it is applied, and may have a thickness that is controlled within a range of, for example, 0.01 ⁇ m to 1000 ⁇ m.
  • the refractive index of the cured film measured at a wavelength of 450 nm using an ellipsometer may be 1.60 or greater.
  • an electronic device including the optical member is provided.
  • an electronic device comprising a cured film of the photopolymerizable composition of some embodiments.
  • the electronic device may be an organic light-emitting device, a solar cell device, an electrochromic material, an electrophoretic device, an organic thin film transistor, or an organic memory device.
  • the cured film of the photopolymerizable composition can be disposed on the front surface of the electronic device, and specifically, can seal the front surface of the electronic device. Specifically, by sealing the front surface of the electronic device, the cured film can increase the refractive index while satisfying the same physical properties as existing devices, thereby increasing the light efficiency of the electronic device (e.g., OLED).
  • OLED organic light efficiency
  • the surface tension of the monomers according to Table 1 below was measured at a temperature of 25°C using a surface tension meter (equipment name: K20 from KRUSS) using the Du Nouy Ring Method or the Wilhelmy Plate Method.
  • the liquid refractive index of the monomers according to Table 1 below was measured at 25°C using a RA-620 measuring device from KEM.
  • Photon initiator C-1 2,4,6-Trimethylbenzoyl-diphenyl-phosphineoxide (Darocur®TPO) C-2 Ethyl(2,4,6-trimethylbenzoyl) phenyphosphinate (Omnirad TPO-L) Surfactant D-1 DowsilTMFZ-2122 D-2 IndusilTMESS-110
  • a photopolymerizable composition was prepared with the composition and content (unit: parts by weight) described in Tables 3 and 4 below.
  • the surface tension of the monomers used in the production of each photopolymerizable composition of the above examples and comparative examples was measured at 25°C using a surface tension meter (equipment name: K20 from KRUSS) by the Du Nouy Ring or Wilhelmy Plate method, and then the deviation of the second monomer with respect to the first monomer was calculated. Specifically, the deviation of the surface tension between the monomers was calculated by the following Equation 1.
  • the absolute viscosity was measured using a viscometer (equipment name: BrookField Viscometer) at a temperature of 25°C.
  • the surface tension of each of the photopolymerizable compositions of the above examples and comparative examples was measured at 25°C using a surface tension meter (equipment name: K20 from KRUSS) using the Du Nouy Ring or Wilhelmy Plate method.
  • Each of the photopolymerizable compositions of the above examples and comparative examples was applied onto a silicon wafer, and then irradiated with UV at an irradiance of 1,500 mJ/cm 2 for 10 seconds to form a cured film (optical film) having a thickness of 2 ⁇ m.
  • the refractive index (wavelength of 450 nm) of the cured film was measured using an ellipsometer.
  • the average transmittance of the cured film formed in the same manner as the above refractive index measurement method was measured at a wavelength (380 to 780 nm) using a UV-vis spectrometer (equipment name: Agilent's Cary4000).
  • a haze meter (COH 400 from NIPPON DENSHOKU) was used.
  • Each of the photopolymerizable compositions of the above examples and comparative examples was ejected using an inkjet device (Unijet OmniJet Series) equipped with a Head (trade name: KM1024i-SHE, Konica Minolta) that ejects droplets quantified as 6 pico liters.
  • A1 is defined as a parameter (unit: ⁇ ) indicating the straightness of the ejected droplets during initial inkjet ejection.
  • A2 is defined as a parameter (unit: °) indicating the straightness of the ejected droplets during continuous ejection or inkjet ejection after long-term standby.
  • the second inkjet droplet characteristics (B2) of the photopolymerizable composition which was left to stand for three days in an inkjet head at a temperature of less than 40°C, were evaluated in the same manner as the first inkjet droplet characteristics.
  • the IDP was calculated by applying the following Equation 2.
  • the units of B1 and B2 are ⁇ m.
  • Fig. 2 shows inkjet droplet parameter results for photopolymerizable compositions according to examples and comparative examples. Referring to Fig. 2, it can be confirmed that the inkjet droplet characteristics of the examples are superior to those of the comparative examples.
  • Example 69 O ⁇ O O O O O O ⁇ ⁇ ⁇ ⁇ Example 70 O ⁇ O O O O O ⁇ ⁇ ⁇ ⁇ Example 71 O ⁇ O O O O ⁇ ⁇ ⁇ ⁇ Example 72 ⁇ ⁇ O O ⁇ ⁇ ⁇ ⁇ O Example 73 ⁇ ⁇ O O ⁇ O ⁇ O ⁇ ⁇ Example 74 ⁇ ⁇ O O O O ⁇ O ⁇ ⁇ Example 75 ⁇ ⁇ O O O O O ⁇ ⁇ ⁇ ⁇ Example 76 ⁇ ⁇ O O O O ⁇ ⁇ ⁇ ⁇ Example 77 ⁇ ⁇ O O ⁇ O ⁇ ⁇ ⁇ ⁇ Example 78 ⁇ ⁇ O O ⁇ O ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une composition photopolymérisable qui améliore les propriétés optiques ainsi que les propriétés de décharge de jet d'encre. Selon un aspect de la présente invention, une composition photopolymérisable comprend : un premier monomère possédant un premier groupe fonctionnel photodurcissable ; un second monomère possédant un second groupe fonctionnel photodurcissable ; et un initiateur, les premier et second monomères satisfaisant l'Expression 1.
PCT/KR2024/006061 2023-05-18 2024-05-07 Composition photopolymérisable et dispositif électronique Pending WO2024237536A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202480027797.6A CN121013872A (zh) 2023-05-18 2024-05-07 光聚合性组合物和电子元件

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2023-0064317 2023-05-18
KR20230064317 2023-05-18
KR10-2024-0059023 2024-05-03
KR1020240059023A KR20240166923A (ko) 2023-05-18 2024-05-03 광중합성 조성물 및 전자소자

Publications (1)

Publication Number Publication Date
WO2024237536A1 true WO2024237536A1 (fr) 2024-11-21

Family

ID=93519840

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2024/006061 Pending WO2024237536A1 (fr) 2023-05-18 2024-05-07 Composition photopolymérisable et dispositif électronique

Country Status (2)

Country Link
CN (1) CN121013872A (fr)
WO (1) WO2024237536A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20010032608A (ko) * 1997-12-05 2001-04-25 그래햄 와일리 광경화성 잉크 젯 잉크 조성물
JP2020056036A (ja) * 2017-03-30 2020-04-09 大日本塗料株式会社 活性エネルギー線硬化型インクジェットインク組成物
KR20220074772A (ko) * 2020-11-27 2022-06-03 주식회사 동진쎄미켐 광중합성 조성물, 이로부터 형성된 광학 부재 및 표시 장치
US20220213335A1 (en) * 2015-09-15 2022-07-07 Maxell, Ltd. Resin composition for modeling material, light curing molding ink set, and method for manufacturing optically shaped article
KR20220104145A (ko) * 2019-11-18 2022-07-26 덴카 주식회사 조성물, 경화체, 유기 전계발광 표시소자용 봉지재 및 유기 전계발광 표시 장치

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20010032608A (ko) * 1997-12-05 2001-04-25 그래햄 와일리 광경화성 잉크 젯 잉크 조성물
US20220213335A1 (en) * 2015-09-15 2022-07-07 Maxell, Ltd. Resin composition for modeling material, light curing molding ink set, and method for manufacturing optically shaped article
JP2020056036A (ja) * 2017-03-30 2020-04-09 大日本塗料株式会社 活性エネルギー線硬化型インクジェットインク組成物
KR20220104145A (ko) * 2019-11-18 2022-07-26 덴카 주식회사 조성물, 경화체, 유기 전계발광 표시소자용 봉지재 및 유기 전계발광 표시 장치
KR20220074772A (ko) * 2020-11-27 2022-06-03 주식회사 동진쎄미켐 광중합성 조성물, 이로부터 형성된 광학 부재 및 표시 장치

Also Published As

Publication number Publication date
CN121013872A (zh) 2025-11-25

Similar Documents

Publication Publication Date Title
WO2015108386A1 (fr) Nouveau composé de β-ester d'oxime fluorène, amorceur de photopolymérisation comprenant ce composé et composition de résine photosensible
WO2017057813A1 (fr) Résine liante et composition de résine photosensible contenant cette dernière
WO2012125009A2 (fr) Composition photosensible positive chimiquement amplifiée pour film isolant organique et procédé l'utilisant pour former un film isolant organique
WO2020111522A1 (fr) Composition de résine photosensible, film et dispositif électronique
WO2020139042A2 (fr) Composé dérivé d'ester d'oxime multi-bêta de carbazole et amorceur de photopolymérisation et composition de résine photosensible comprenant ledit composé
WO2015016456A1 (fr) Film de retardement et dispositif d'affichage d'images présentant un tel film
WO2022260283A1 (fr) Composition de résine photosensible, film de résine photosensible l'utilisant, filtre coloré et dispositif d'affichage
WO2013051831A2 (fr) Composition de formation d'une couche d'alignement et couche d'alignement et film de différence de phase fabriqués à l'aide de celle-ci
WO2013100276A1 (fr) Composition de résine photosensible pour filtre coloré et filtre coloré utilisant celle-ci
WO2014065517A1 (fr) Composition de résine durcissante et film optique fabriqué avec cette composition
WO2015064958A1 (fr) Nouveau composé de biphényle d'ester d'oxime, photo-initiateur et composition de résine photosensible le contenant
WO2011052934A2 (fr) Composition d'encre pour jet d'encre pour la formation d'un film transparent et procédé de préparation d'une telle composition
WO2024237536A1 (fr) Composition photopolymérisable et dispositif électronique
WO2020197179A1 (fr) Copolymère soluble dans les alcalis, photodurcissable et thermodurcissable, et composition de résine photosensible, film de résine photosensible et filtre coloré l'utilisant
WO2019074262A1 (fr) Résine liante et composition de résine photosensible ou solution de revêtement la contenant
WO2014168393A1 (fr) Composition de film isolant hybride organique-inorganique photosensible de type négatif
WO2021210783A1 (fr) Composition de résine photosensible, et film de résine photosensible ainsi que filtre coloré fabriqués en l'utilisant
WO2021256814A1 (fr) Composition d'encapsulation et diode électroluminescente
WO2022065886A1 (fr) Composition thermodurcissable à faible indice de réfraction, élément optique formé à partir de cette dernière et appareil d'affichage
WO2021132865A1 (fr) Composé de résine polymère, son procédé de production, et composition de résine photosensible le comprenant
WO2022114837A1 (fr) Composition photopolymérisable, élément optique préparé à partir de celle-ci, et dispositif d'affichage
WO2023022452A1 (fr) Composition de résine photosensible et dispositif d'affichage
WO2024167235A1 (fr) Composition photopolymérisable pour jet d'encre, film durci de celle-ci, et élément optique et dispositif d'affichage la comprenant
WO2018199450A1 (fr) Composition photo-durcissable pour revêtement et film de revêtement
WO2025009699A1 (fr) Composition durcissable, film durci préparé à l'aide de ladite composition, et dispositif d'affichage comprenant ledit film durci

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24807413

Country of ref document: EP

Kind code of ref document: A1