Photopolymerizable compositions and electronic devices
The photopolymerizable composition addresses surface hardening issues in optical films by controlling surface tension and refractive index, improving inkjet ejection and optical properties while reducing haze.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- DONGJIN SEMICHEM CO LTD
- Filing Date
- 2024-05-07
- Publication Date
- 2026-05-21
AI Technical Summary
Existing photopolymerizable compositions used to form optical films suffer from insufficient surface hardening due to oxygen inhibition, leading to increased haze, reduced light transmittance, and decreased mechanical properties, which are unsuitable for high flexibility and bending reliability, especially in foldable devices.
A photopolymerizable composition comprising specific monomers with controlled surface tension and refractive index, along with an initiator, to enhance inkjet ejection characteristics, refractive index, and optical properties, while minimizing haze.
The composition achieves improved inkjet ejection, higher refractive index, and increased light transmittance with reduced haze, resulting in enhanced optical components and mechanical properties.
Smart Images

Figure 2026516319000001_ABST
Abstract
Description
[Technical Field]
[0001] The present invention relates to photopolymerizable compositions, and more specifically to photopolymerizable compositions, optical components, and electronic devices. [Background technology]
[0002] In the case of a light-transmitting optical film having a structured prism, the rate of brightness increase changes depending on the refractive index of the resin forming the prism structure. Generally, the higher the refractive index of the resin constituting the prism, the higher the rate of brightness increase. For this reason, research and development of the aforementioned light-transmitting optical film is progressing in the direction of increasing the refractive index of the resin forming the prism structure.
[0003] When using existing general photopolymerizable compositions as monomer compositions to form the aforementioned resins and optical films, surface hardening often did not occur sufficiently during the photocuring process of the monomer compositions due to the influence of oxygen in the air. As a result, the resins and optical films suffered from increased haze, leading to problems such as reduced light transmittance (including UV transmittance) and decreased visibility.
[0004] Furthermore, insufficient surface hardening degrades the mechanical properties of the film, significantly reducing the high flexibility and bending reliability required for foldable devices. Therefore, considering these problems, a method of carrying out the hardening process under an inert gas atmosphere such as nitrogen has been considered, but this can lead to a significant increase in manufacturing costs.
[0005] Due to the aforementioned problems, while the material exhibits viscosity characteristics suitable for inkjet processes, it has not been developed to a satisfactory level in terms of excellent optical properties and high flexibility. Therefore, the development of technologies that enable the formation of optical films and other materials exhibiting excellent optical and mechanical properties is continuously needed. [Overview of the Initiative] [Problems that the invention aims to solve]
[0006] The object of the present invention is to provide a photopolymerizable composition that improves inkjet ejection characteristics.
[0007] Another object of the present invention is to provide a photopolymerizable composition that increases the refractive index and transmittance of optical components and reduces haze.
[0008] Another object of the present invention is to provide an optical component obtained by curing the photopolymerizable composition.
[0009] Another object of the present invention is to provide an electronic element including the optical element.
[0010] The objectives of the present invention are not limited to those mentioned above, and other objectives and advantages of the present invention not mentioned will be understood from the following description and will be more clearly understood from the embodiments of the present invention. Furthermore, it will be readily apparent that the objectives and advantages of the present invention can be achieved by the means and combinations set forth in the claims. [Means for solving the problem]
[0011] To achieve the above objective, according to a first aspect of the present invention, a photopolymerizable composition is provided 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.
[0012] [Formula 1]
[0013] C = |AB| ≤ 8.0 mN / m
[0014] In Equation 1, C is the absolute value (mN / m) of the deviation of the surface tension of the second monomer from the surface tension of the first monomer, A is the surface tension (mN / m) of the first monomer at 25°C, and B is the surface tension (mN / m) of the second monomer at 25°C.
[0015] According to a second aspect of the present invention, in the first aspect, the liquid refractive index of the first monomer may be 1.57 or greater.
[0016] According to a third aspect of the present invention, in the first or second aspect, the surface tension of the first monomer may be 41 mN / m or less.
[0017] According to a fourth aspect of the present invention, in any one of the first to third aspects, the first monomer may include an aromatic compound containing one or more aromatic ring structures or one or more heteroatoms.
[0018] According to a fifth aspect of the present invention, in any one of the first to fourth aspects, the first monomer may include a structure represented by the following chemical formula 1.
[0019] [C1]
[0020] JPEG2026516319000002.jpg11170
[0021] In the above chemical formula 1, A comprises one or more structures from among a substituted or unsubstituted aryl group; a substituted or unsubstituted aromatic heterocycle; and a substituted or unsubstituted bicyclic; X1 is a directly bonded or divalent linking group having 1 to 20 carbon atoms with or without one or more oxygen atoms; X2 is a directly bonded or divalent linking group having 1 to 20 carbon atoms with or without one or more oxygen atoms; and R is the first photocurable functional group. Specifically, the substituted or unsubstituted bicyclic may be a bridged bicyclic structure. For example, the divalent linking groups in X1 and X2 that do not contain oxygen atoms may include at least one of alkylene groups, alkenylene groups, and alkynylene groups.
[0022] According to the sixth aspect of the present invention, in the fifth aspect, in Chemical Formula 1, A is a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, X1 is a direct bond, and X2 may be a divalent linking group having 1 to 10 carbon atoms that contains or does not contain one or more oxygen atoms.
[0023] According to the seventh aspect of the present invention, in any one of the first to sixth aspects, the first monomer may contain any one or more selected from the group consisting of benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxybenzyl (meth)acrylate, O-phenylphenoxyethyl (meth)acrylate, biphenyl (meth)acrylate, biphenyl ethyl (meth)acrylate, and compounds represented by the following Chemical Formulas 2 to 9.
[0024] [Chemical Formula 2]
[0025] JPEG2026516319000003.jpg34170
[0026] [Chemical Formula 3]
[0027] JPEG2026516319000004.jpg39170
[0028] [Chemical Formula 4]
[0029] JPEG2026516319000005.jpg43170
[0030] [Chemical Formula 5]
[0031] JPEG2026516319000006.jpg37170
[0032] [Chemical Formula 6]
[0033] JPEG2026516319000007.jpg66170
[0034] [Chemical Formula 7]
[0035] JPEG2026516319000008.jpg18170
[0036] [8]
[0037] JPEG2026516319000009.jpg17170
[0038] [9]
[0039] JPEG2026516319000010.jpg16170
[0040] In the chemical formulas 2 to 9 above, R is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and n is independently a constant from 0 to 10. For example, n may independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
[0041] According to the eighth aspect of the present invention, in any one of the first to seventh aspects, the purity of the first monomer may be 95% or higher.
[0042] According to the ninth aspect of the present invention, in any one of the first to eighth aspects, the purity of the first monomer may be 98% or higher.
[0043] According to the tenth aspect of the present invention, in any one of the first to ninth aspects, the content of the first monomer may be 30 to 90 parts by weight with respect to 100 parts by weight of the total monomer including the first monomer and the second monomer.
[0044] According to the eleventh aspect of the present invention, in any one of the first to tenth aspects, the second monomer may include a structure represented by the following chemical formula 10.
[0045] [C10]
[0046] JPEG2026516319000011.jpg12170
[0047] In the chemical formula 10, B and B' comprise the same or different second photocurable functional group, Y comprises a substituted or unsubstituted hydrocarbon structure having 4 to 50 carbon atoms, with or without one or more oxygen atoms, and n and m are each independently integers from 0 to 2, satisfying n+m=1 or 2. Here, Y may include, for example, a divalent linking group in which all atoms linked to the second photocurable functional group are oxygen atoms, specifically -O-(CH2)xO-. For example, x may be 1 or more, specifically 1, 2, 3, 4, 5, 6, 7, 8, or 9.
[0048] According to a twelfth aspect of the present invention, in the eleventh aspect, in the chemical formula 10, 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.
[0049] According to a thirteenth aspect of the present invention, in any one of the first to twelfth aspects, the second monomer may include one or more compounds 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 compounds represented by the following chemical formula 11.
[0050] [C11]
[0051] JPEG2026516319000012.jpg21170
[0052] In the chemical formula 11, R is independently either hydrogen or an alkyl group, and a, b, and c are integers satisfying a+b+c=1 to 20. For example, the alkyl group may be a linear or branched alkyl group having 1 to 5 carbon atoms.
[0053] According to a fourteenth aspect of the present invention, in the thirteenth aspect, in the chemical formula 11, b is 0, and a and c may be integers from 1 to 20.
[0054] According to a 15th aspect of the present invention, in any one of the 1st to 14th aspects, the content of the initiator may be 0.5 to 10 parts by weight with respect to 100 parts by weight of the total monomer including the first monomer and the second monomer.
[0055] According to a sixteenth aspect of the present invention, in any one of the first to fifteenth aspects, the initiator may include a radical initiator.
[0056] According to a 17th aspect of the present invention, a photopolymerizable composition can be provided that further comprises one or more selected from the group consisting of surfactants, amine enhancers, and photosensitizers, in any one of the first to 16th aspects.
[0057] According to the eighteenth aspect of the present invention, in the seventeenth aspect, the amount of the surfactant may be 0.001 to 20 parts by weight per 100 parts by weight of the total monomers including the first monomer and the second monomer.
[0058] According to the 19th aspect of the present invention, a photopolymerizable composition in a solvent-free form can be provided in any one of the first to 18 aspects described above.
[0059] According to the 20th aspect of the present invention, in any one of the first to 19 aspects, a photopolymerizable composition can be provided having an absolute viscosity of 5 to 40 cP measured at 25°C.
[0060] According to the 21st aspect of the present invention, an optical member can be provided that includes a cured film obtained by curing a photopolymerizable composition according to any one of the 1st to 20th aspects.
[0061] According to a 22nd aspect of the present invention, in the 21st aspect, the haze of the cured film may be 3% or less, and the average transmittance within the wavelength range of 380 to 720 nm may be 95% or more.
[0062] According to a 23rd aspect of the present invention, an electronic element including an optical member according to the 21st or 22nd aspect is provided.
[0063] The means for solving the above problems do not constitute a complete list of all features of the present invention. The diverse features of the present invention and their advantages and effects will be understood in more detail by referring to the following specific examples. [Effects of the Invention]
[0064] According to one aspect of the present invention, the viscosity and surface tension of the photopolymerizable composition can be controlled to appropriate levels, thereby improving the ink ejection characteristics from the nozzles of the inkjet head.
[0065] According to another aspect of the present invention, a photopolymerizable composition can improve the optical properties of a cured optical component by increasing its refractive index and light transmittance and lowering its haze value.
[0066] Along with the effects described above, the specific effects of the present invention will be described in conjunction with the following explanation of embodiments for carrying out the invention. [Brief explanation of the drawing]
[0067] [Figure 1] These are the results of the inkjet ejection characteristics for photopolymerizable compositions in the examples and comparative examples.
[0068] [Figure 2] These are the results of the inkjet droplet parameters for photopolymerizable compositions in the examples and comparative examples. [Modes for carrying out the invention]
[0069] In this specification, singular expressions include plural expressions unless the context clearly indicates otherwise.
[0070] In this specification, the terms “Comprise” and / or “Comprising” identify the presence of the shapes, stages, figures, actions, members, elements and / or groups thereof mentioned, and do not exclude the presence or addition of one or more other shapes, stages, figures, actions, members, elements and / or groups thereof.
[0071] In this specification, "at least one of a, b and c" may include a, b, or c individually, or two or more combinations selected from the group consisting of a, b, and c.
[0072] Where various embodiments are described herein, unless otherwise specified, each embodiment can be combined. In this case, the effects of the present invention can be defined as including the effects that originate from each embodiment and the effects that result from the organic combination of each embodiment. For example, even if Examples 1 and 2 are described independently herein, Examples 1 and 2 may be combined organically with each other unless the context clearly means otherwise, and the effects of the present invention may include the effects that result from the combination of Examples 1 and 2.
[0073] In this specification, a range of numbers indicated using the term "~" refers to a range of numbers that includes the values described before and after the term as the lower and upper limits, respectively. If multiple numbers are disclosed as upper and lower limits for any given range of numbers, the range of numbers disclosed in this specification can be understood as any range of numbers whose lower limit and upper limit are any one of the multiple lower limits and any one of the multiple upper limits, respectively. For example, if the specification states a~b or c~d, it can be understood as describing a range between a and b, a and d, c and d, or c and b.
[0074] In this specification, a “layer” or “film” may include cases where, when observing the region in which the layer or film exists, it is formed not only over the entire region but also over only a portion of the region. For example, the surface of the layer or film may be defined as having a flattened form, a non-flattened form, and a combination thereof; or a continuous form, a discontinuous form, and a combination thereof. For example, when one member is directly on top of another member, the coverage of the other member over the surface of the first 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. For example, when multiple particles are clustered together to form a structure, it may also be defined as a “layer” or “film”.
[0075] In this specification, the "weight average molecular weight" or "number average molecular weight" is the molecular weight in terms of standard polystyrene and can be analyzed by a GPC (Gel permeation chromatography) apparatus. For example, in the case of the GPC analysis method, the eluent is tetrahydrofuran (THF), the column is PL Olexis from Polymer Laboratories, the sample concentration is 5 mg / mL, the sample injection volume is 100 μL, the flow rate is 1 mL / min, the detector is an Agilent High Temperature RI detector, and the column temperature can be set at 40°C.
[0076] In this specification, "substituted", unless otherwise defined below, means that at least one or more hydrogen atoms are replaced by any one selected from the group consisting of a halogen atom, a hydroxy 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, an alkyl group having C1 - C 30 of an alkyl group, an alkenyl group having C2 - C 30 of an alkenyl group, an alkynyl group having C2 - C 30 of an alkynyl group, an alkylsilyl group having C1 - C 40 of an alkylsilyl group, an arylsilyl group having C5 - C 40 of an arylsilyl group, a cycloalkyl group having C3 - C 30 of a cycloalkyl group, an allyl group having C3 - C 30 of an allyl group, an aryl group having C6 - C 30 of an aryl group, a heterocyclic group (e.g., a heterocycloalkyl group having C2 - C 30 of a heterocycloalkyl group, a heteroaryl group having C3 - C 30 of a heteroaryl group), derivatives thereof, and any one combination selected from the group consisting thereof. Here, when the respective substituents are adjacent to each other, they may combine with each other to form a substituted or unsubstituted fused ring or spiro structure.
[0077] In this specification, "Fused ring" means a ring in which two or more rings are bonded together by sharing two or more atoms, and may include, for example, fused aliphatic rings, fused aromatic rings, fused heteroaliphatic rings, fused heteroaromatic rings, or combinations thereof.
[0078] In this specification, "spiro structure" means having a spiro union, which is a linkage in which two rings share only one atom.
[0079] In this specification, "meth(acrylate)" may be defined as including acrylates or methacrylate groups.
[0080] According to one aspect of the present invention, a photopolymerizable composition is provided 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.
[0081] [Formula 1]
[0082] C = |AB| ≤ 8.0 mN / m
[0083] In Formula 1, C is the absolute value (mN / m) of the deviation of the surface tension of the second monomer from the surface tension of the first monomer, A is the surface tension (mN / m) of the first monomer at 25°C, and B is the surface tension (mN / m) of the second monomer at 25°C. According to one aspect of the present invention, by satisfying the range of 8.0 mN / m or less for the absolute value (mN / m) of the deviation of the surface tension of the second monomer from the surface tension of the first monomer, the viscosity and surface tension of the photopolymerizable composition are controlled to appropriate levels, allowing ink to be ejected smoothly from the nozzle of the inkjet head without clogging. According to another aspect of the present invention, by satisfying the range of 8.0 mN / m or less for the absolute value (mN / m) of the deviation of the surface tension of the second monomer from the surface tension of the first monomer, an optical component with a higher refractive index, lower haze value, and high light transmittance can be realized.
[0084] The configuration of the present invention will be described in more detail below.
[0085] 1. Photopolymerizable composition
[0086] First monomer
[0087] The photopolymerizable composition according to the present invention comprises a first monomer having a first photocurable functional group that can increase the refractive index of an optical component.
[0088] Specifically, the first photocurable functional group may include a reactive functional group that can undergo photopolymerization in the presence of an initiator. For example, the first photocurable functional group may include any one selected from the group consisting of a (meth)acrylic group, a carbon-carbon unsaturated bond, and combinations thereof. Specifically, the carbon-carbon unsaturated bond may be a carbon-carbon double bond or a carbon-carbon triple bond. Here, the first monomer may contain at least one of these carbon-carbon unsaturated bonds. Here, the (meth)acrylic group may be an unsaturated carbonyl group containing 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)acrylic group].
[0089] According to one embodiment of the present invention, the liquid refractive index of the first monomer may be 1.57 or higher, more specifically 1.57 to 1.65, and more specifically 1.58 to 1.63. By satisfying the above numerical range for the liquid refractive index of the first monomer, the refractive index of the cured film due to ultraviolet irradiation or the like can be increased.
[0090] According to one embodiment of the present invention, 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 37.8 mN / m or less, and more specifically, it may be 37 mN / m or more and less than or equal to any one of the above multiple values. Specifically, by satisfying the above numerical range for the surface tension of the first monomer, when the photopolymerizable composition is used as an ink in an inkjet printer, an effect of excellent ejection characteristics can be further realized, and the ejected photopolymerizable composition can be sufficiently cured. For example, the surface tension of the first monomer can be measured at 25°C using a surface tension meter (device name: K20 from KRUSS) using the Du Nouy Ring or Wilhelmy Plate method.
[0091] According to one embodiment of the present invention, the first monomer may include one or more aromatic ring structures or aromatic compounds containing one or more heteroatoms. Specifically, by including one or more aromatic ring structures or aromatic compounds containing one or more heteroatoms in the first monomer, the optical properties of the optical member can be improved, and at the same time, the surface tension and viscosity of the photopolymerizable composition can be controlled to appropriate levels, thereby further improving the ink ejection characteristics.
[0092] According to one embodiment of the present invention, the first monomer may have a structure represented by the following chemical formula 1.
[0093] [C1]
[0094] JPEG2026516319000013.jpg11170
[0095] In the above chemical formula 1, A comprises one or more structures of any of the following: a substituted or unsubstituted aryl group; a substituted or unsubstituted aromatic heterocycle; and a substituted or unsubstituted bridged bicyclic; X1 is a directly bonded or divalent linking group having 1 to 20 carbon atoms with or without one or more oxygen atoms; X2 is a directly bonded or divalent linking group having 1 to 20 carbon atoms with or without one or more oxygen atoms; and R is the first photocurable functional group.
[0096] For example, in A, the aryl group may contain one or more, two or more, or three or more benzene rings. Here, the benzene rings may be substituted or unsubstituted. For example, the aromatic heteroring may be an aromatic ring containing one or more heteroatoms, specifically an aromatic ring containing any one selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, and combinations thereof. For example, in the bridging biring structure, two rings may share two carbon atoms, and one or more hydrogen atoms bonded to the matrix of the bridging biring structure may be substituted with a functional group including a carboxyl group.
[0097] In some examples, the crosslinked bicyclic structure may include a fused aromatic ring, specifically a naphthalene group, anthracene group, phenanthrene group, perylene group, or tetracene group.
[0098] For example, in X1, a divalent linking group having 1 to 20 carbon atoms and containing one or more oxygen atoms may include one or more of the following: an ester group (-COO- or -OOC-), an ether group (-O-), and a ketone group (-CO-). Specifically, the divalent linking group may include one or more of the following: an aliphatic structure having 1 to 20 carbon atoms and an aromatic structure. More specifically, the aliphatic structure may include any one selected from the group consisting of aliphatic chain structures, aliphatic cyclic structures, and combinations thereof, satisfying the carbon number range described above. The aromatic structure may include any one selected from the group consisting of aryl groups, heteroaryl groups, and combinations thereof, satisfying the carbon number range described above.
[0099] For example, in X2, a divalent linking group having 1 to 20 carbon atoms and containing one or more oxygen atoms may include one or more of the following: an ester group (-COO- or -OOC-), an ether group (-O-), and a ketone group (-CO-). Specifically, the divalent linking group may include one or more of the following: an aliphatic structure having 1 to 20 carbon atoms and an aromatic structure. More specifically, the aliphatic structure may include any one selected from the group consisting of aliphatic chain structures, aliphatic cyclic structures, and combinations thereof, satisfying the carbon number range described above. The aromatic structure may include any one selected from the group consisting of aryl groups, heteroaryl groups, and combinations thereof, satisfying the carbon number range described above.
[0100] According to one embodiment of the present invention, in the chemical formula 1, A is a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, X1 is a direct bond, and X2 may be a divalent linking group having 1 to 10 carbon atoms containing or not containing one or more oxygen atoms. Specifically, it may be a divalent linking group having 1 to 10 carbon atoms containing one or more oxygen atoms. Specifically, by satisfying the conditions in the chemical formula 1, where A is a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, X1 is a direct bond, and X2 is a divalent linking group having 1 to 10 carbon atoms containing one or more oxygen atoms, the optical properties of the optical component (e.g., high refractive index and low haze) can be improved, and at the same time, the surface tension and viscosity of the photopolymerizable composition can be controlled to appropriate levels, further improving the inkjet ejection characteristics.
[0101] For example, the first monomer may contain one or more compounds selected from the group consisting of benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxybenzyl (meth)acrylate, O-phenylphenoxyethyl (meth)acrylate, biphenyl (meth)acrylate, biphenylethyl (meth)acrylate, and compounds represented by the following chemical formulas 2 to 9.
[0102] [C2]
[0103] JPEG2026516319000014.jpg34170
[0104] The compound represented by chemical formula 2 may contain one or more selected from the groups represented by chemical formulas 2-1 and 2-2.
[0105] [C3]
[0106] JPEG2026516319000015.jpg39170
[0107] The compound represented by chemical formula 3 may contain one or more selected from the group represented by chemical formulas 3-1 to 3-3.
[0108] [C4]
[0109] JPEG2026516319000016.jpg43170
[0110] The compound represented by chemical formula 4 may contain one or more selected from the group represented by chemical formulas 4-1 to 4-3.
[0111] [5]
[0112] JPEG2026516319000017.jpg37170
[0113] The compound represented by chemical formula 5 may contain one or more selected from the group represented by chemical formulas 5-1 to 5-2.
[0114] [6]
[0115] JPEG2026516319000018.jpg66170
[0116] The compound represented by chemical formula 6 may contain one or more compounds selected from the group represented by chemical formulas 6-1 to 6-6.
[0117] [7]
[0118] JPEG2026516319000019.jpg18170
[0119] [8]
[0120] JPEG2026516319000020.jpg17170
[0121] [9]
[0122] JPEG2026516319000021.jpg16170
[0123] In the chemical formulas 2 to 9, R is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and n is independently an integer from 0 to 10. For example, in the chemical formulas 2 to 9, n may independently be 0.1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
[0124] According to one embodiment of the present invention, the purity of the first monomer may be 94% or higher, 95% or higher, 96% or higher, specifically 98% or higher, and more specifically 98.01% to 99.99%. Specifically, by satisfying the above numerical range for the purity of the first monomer, the inkjet ejection characteristics and inkjet droplet parameter characteristics can be further improved. More specifically, even if the purity of the first monomer satisfies the above range, if the absolute value (mN / m) of the deviation of the surface tension of the second monomer from the surface tension of the first monomer exceeds 8.0 mN / m, a problem may arise in which the ejection characteristics of the photopolymerizable composition cannot be sufficiently improved. For example, the purity of the first monomer can be measured using liquid chromatography or gas chromatography.
[0125] According to one embodiment of the present invention, 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 monomer including the first monomer and the second monomer. By satisfying the above numerical range for the content of the first monomer, the optical properties of the optical component (e.g., high refractive index and low haze) can be improved, and at the same time, the surface tension and viscosity of the photopolymerizable composition can be controlled to appropriate levels, further improving the inkjet ejection characteristics.
[0126] Second monomer
[0127] The photopolymerizable composition according to the present invention includes a second monomer having a second photocurable functional group in order to reduce the viscosity of the photopolymerizable composition and to adjust the curing rate and degree of curing of the photopolymerizable composition. Specifically, the second photocurable functional group may be the same as or different from the first photocurable functional group described above.
[0128] Specifically, the second monomer may include a structure represented by the following chemical formula 10, and more specifically, it may include a compound represented by the following chemical formula 10.
[0129] [C10]
[0130] JPEG2026516319000022.jpg12170
[0131] In the above chemical formula 10, B and B' comprise the same or different second photocurable functional group, Y comprises a substituted or unsubstituted hydrocarbon structure having 4 to 50 carbon atoms, with or without one or more oxygen atoms, and n and m are integers from 0 to 2, satisfying n+m=1 or 2.
[0132] For example, in the chemical formula 10, if Y includes a substituted or unsubstituted hydrocarbon structure having 4 to 50 carbon atoms containing one or more oxygen atoms, Y may be a divalent linking group (-O-Rm-O-) containing oxygen atoms at one end (-O-Rm- or -Rm-O-) or both ends. Here, Rm may be a linear or branched alkylene group having 4 to 50 carbon atoms, with or without containing one or more ether groups.
[0133] According to one embodiment of the present invention, in the chemical formula 10, Y is an aliphatic or aromatic structure having 4 to 50 carbon atoms, and can 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. According to one embodiment of the present invention, by including the structure represented by chemical formula 10 in the second monomer, the absolute value (mN / m) of the deviation of the surface tension of the second monomer from the surface tension of the first monomer can be satisfied as 8.0 mN / m or less. This allows the viscosity and surface tension of the photopolymerizable composition to be controlled to an appropriate level, enabling ink to be ejected smoothly from the nozzle of the inkjet head. According to another embodiment of the present invention, it is possible to realize an optical component with a higher refractive index, a lower haze value, and high light transmittance.
[0134] For example, the second monomer may contain one or more compounds 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 compounds represented by the following chemical formula 11.
[0135] [C11]
[0136] JPEG2026516319000023.jpg21170
[0137] In the chemical formula 11, R is independently either hydrogen or an alkyl group, and a, b, and c are integers satisfying a+b+c=1 to 20. More specifically, in the chemical formula 11, b may be 0, and a and c may be integers from 1 to 20. For example, the alkyl group may be a linear or branched alkyl group having 1 to 5 carbon atoms.
[0138] According to one embodiment of the present invention, 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 monomer including the first monomer and the second monomer. By satisfying the above numerical range for the content of the second monomer, the viscosity and surface tension of the photopolymerizable composition are controlled to appropriate levels, and the photopolymerizable composition can exhibit excellent ejection characteristics when applied to inkjet printing ink.
[0139] According to one embodiment of the present invention, the surface tension of the second monomer measured at 25°C may be 30 mN / m or more, more specifically 31 to 40 mN / m, and more specifically 32.8 to 39.3 mN / m. By satisfying the above numerical range for the surface tension of the second monomer, the viscosity and surface tension of the photopolymerizable composition are controlled to appropriate levels, and when the photopolymerizable composition is applied to inkjet printing ink, it can exhibit excellent ejection characteristics.
[0140] Relationship between the first and second monomers
[0141] According to one aspect of the present invention, a photopolymerizable composition is provided 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.
[0142] [Formula 1]
[0143] C = |AB| ≤ 8.0 mN / m
[0144] In Formula 1, C is the absolute value (mN / m) of the deviation of the surface tension of the second monomer from the surface tension of the first monomer, A is the surface tension (mN / m) of the first monomer at 25°C, and B is the surface tension (mN / m) of the second monomer at 25°C. According to one aspect of the present invention, by satisfying the range of 8.0 mN / m or less for the absolute value (mN / m) of the deviation of the surface tension of the second monomer from the surface tension of the first monomer, the viscosity and surface tension of the photopolymerizable composition are controlled to appropriate levels, allowing ink to be ejected well from the nozzles of the inkjet head. According to another aspect of the present invention, by satisfying the range of 8.0 mN / m or less for the absolute value (mN / m) of the deviation of the surface tension of the second monomer from the surface tension of the first monomer, an optical component with a higher refractive index, lower haze value, and high light transmittance can be realized.
[0145] Specifically, in Formula 1, C can satisfy the condition of being 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 Formula 1, the viscosity and surface tension of the photopolymerizable composition can be controlled, further improving the ink ejection characteristics from the nozzles of the inkjet head.
[0146] Initiator
[0147] The photopolymerizable composition according to the present invention comprises an initiator to initiate and accelerate the photocuring reaction of the first monomer and the second monomer described above.
[0148] The initiator content 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 monomer including the first monomer and the second monomer. When the initiator content satisfies the above numerical range, the photocuring reaction is carried out sufficiently, and at the same time, the transmittance of the cured film obtained by curing the photopolymerizable composition can be sufficiently high.
[0149] For example, the initiator may include a radical initiator that induces a photopolymerization reaction via a radical mechanism.
[0150] In other embodiments of the present invention, the weight ratio of the initiator to the first monomer (initiator:first monomer) may be 1:5 to 1:120. Specifically, by satisfying the above numerical range for the weight ratio of the initiator to the first monomer (initiator:first monomer), the photocuring reaction can be carried out sufficiently, and at the same time, the transmittance of the cured film obtained by curing the photopolymerizable composition can be sufficiently high.
[0151] According to yet another embodiment of the present invention, the weight ratio of the initiator to the second monomer (initiator:second monomer) may be 1:3 to 1:90. Specifically, by satisfying the above numerical range for the weight ratio of the initiator to the second monomer (initiator:second monomer), the photocuring reaction can be carried out sufficiently, and at the same time, the transmittance of the cured film obtained by curing the photopolymerizable composition can be sufficiently high.
[0152] For example, the initiator, 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-diphenylimidazole dimer, 2-(o-chlorophenyl)-4,5-di(m-methoxyphenyl [1-[9-Ethylimidazole dimer, 2-(o-fluorophenyl)-4,5-diphenylimidazole dimer, 2-(-o-methoxyphenyl)-4,5-diphenylimidazole dimer, 2,4-di(p-methoxyphenyl)-5-phenylimidazole dimer, 2-(2,4-dimethoxyphenyl)-4,5-diphenylimidazole dimer, 2-(p-methylmercaptophenyl)-4,5-diphenylimidazole dimer, [1-[9-Ethylimidazole dimer] Lu-6-(2-methylbenzoyl)-9H-carbazoyl-3-yl]-1-(0-acetyloxime), benzophenone, p-(diethylamino)benzophenone, 2,2-dichloro-4-phenoxyacetophenone, 2,2-diethoxyacetophenone, 2-dodecylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,2-bis-2-chlorophenyl, 4,5,4,5-tetraphenyl-2-1, 2-biimidazole, (E)-2-(acetoxyimino)-1-(9,9-diethyl-9H-fluoren-2-yl)butanone, (E)-1-(9,9-dibutyl)-7-nitro-9H-fluoren-2-yl]-ethanone 0-acetyloxime, (Z)-2-(acetoxyimino)-1-(9,9-diethyl-9H-fluoren-2-yl)propanone, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, ethyl(2,4,6-Trimethylbenzoyl)phenylphosphinate, IRGACURE184, IRGACURE500, IRGACURE2959, DAROCURE1173, IRGACURE754, DAROCUREMBF, IRGACURE651, IRGACURE369, IRGACURE907, IRGACURE1300, DAROCURETPO, OmniradTPO-L, IRGACURE819, IRGACURE It may contain one or more compounds selected from the group consisting of benzoin-based, benzophenone-based, imazole-based, phenylglyoxylate-based, xanthone-based, oxime ester-based, acetophenone-based, hydroxyketone-based, aminoketone-based, benzyldimethyl-based, monoacylphosphine-based, bisacylphosphine-based, metallocene-based, iodonium salt-based, or phosphine oxide-based compounds, including 819DW, IRFACURE2100, IRGACURE784, IRGACURE250, OXE-01, OXE-02, OXE-03, OXE-04, N-1919, NCI-831, NCI-930, etc.
[0153] additives
[0154] The photopolymerizable composition according to the present invention may further contain one or more selected from the group consisting of surfactants, amine enhancers, and photosensitizers, and specifically may contain a surfactant.
[0155] The surfactant according to the present invention can improve the uniformity of the thickness and surface smoothness of the cured film obtained by curing a photopolymerizable composition.
[0156] Specifically, the amount of the surfactant may be 0.001 to 20 parts by weight, 0.001 to 5 parts by weight, 0.01 to 0.05 parts by weight, or 0.03 to 0.05 parts by weight per 100 parts by weight of the total monomer including the first monomer and the second monomer. By satisfying the above numerical range for the amount of the surfactant, the uniformity of the thickness and surface smoothness of the cured film can be improved, and at the same time, the formation of air bubbles inside the film can be effectively prevented, thereby further improving the inkjet ejection characteristics.
[0157] For example, the surfactants include BM-1000, BM-1100 (BM CHEMIE), Megafac F-142D, F-172, F-173, F-183, F-470, F-471, F-475, F-482 and F-489 (Dainippon Ink and Chemicals, Inc.), Florard FC-135, FC-170C, FC-430, FC-431 (Sumitomo 3M), F-Top EF301, EF303 and EF352 (Shin Akita Chemical Co., Ltd.), Surflon S-112, S-131, S-141, S-145, S-382, SC-101, SC-102, SC-103, SC-104, SC-105, SC-106 (Asahi Glass Co., Ltd.), SH-28 PA, SH-190, SH-193, SZ-6032, SF-6032, SF-8428, DC-57, DC-190 (Toray Silicone Co.), DC3PA, DC7PA, SH11PA, SH21PA, SH8400, FZ-2100, FZ-2110, FZ-2122, FZ-2222, FZ-2233 (Dow Corning Toray Silicone Co.), TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, TSF-4452 (GD Toshiba Silicone Co.), BYK-333 (BYK Co.), ESS-110, ESS-210, ESS-310 and CoatOSil It may contain one or more surfactants from the group consisting of: fluorine-based and silicone-based surfactants such as Series (Momentive); polyethylene oxyalkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and polyoxyethylene oleyl ether; polyoxyethylene aryl ethers such as polyethylene octylphenyl ether and polyoxyethylene nonylphenyl ether; and polyoxyethylene dialkyl esters such as polyethylene dilaurate and polyoxyethylene distearate; and (meth)acrylic acid copolymers such as organosiloxane polymer KP341 (Shin-Etsu Chemical Co., Ltd.), No. 57, and 95 (Kyoeisha Oil & Fat Chemical Industry Co., Ltd.).
[0158] The amine enhancer according to the present invention can increase the surface hardness of the cured film while simultaneously reducing the haze of the optical component. Specifically, the amine group of the amine enhancer can capture oxygen radicals in the air and promote the reaction of the initiator. Furthermore, if the amine enhancer has a photocurable functional group, it may form crosslink bonds with the first and second monomers described above. For example, the amine enhancer is not particularly limited and may include ethyldimethylaminobenzoate, butoxyethyldimethylaminobenzoate, diethylaminoethyl (meth)acrylate, etc.
[0159] The photosensitizer according to the present invention can promote a photopolymerization reaction. For example, the photosensitizer may contain one or more from the group consisting of isopropylthioxanthone, pyrene, perylene, triphenylene, anthracene, 9,10-dibutoxyanthracene, 9,10-diethoxyanthracene, 3,7-dimethoxyanthracene, and 9,10-dipropyloxyanthracene.
[0160] Physical properties of photopolymerizable compositions
[0161] In some embodiments of the present invention, the photopolymerizable composition may be in a solvent-free form that does not contain a solvent. Specifically, the photopolymerizable composition may have an absolute viscosity of 5 to 40 cP as measured at 25°C. By satisfying the above numerical range for the absolute viscosity of the photopolymerizable composition, the inkjet ejection characteristics can be improved. For example, the absolute viscosity of the photopolymerizable composition can be measured at 25°C using a viscometer (device name: Brookfield Viscometer).
[0162] In some embodiments of the present invention, the inkjet droplet parameter (IDP) of the photopolymerizable composition may be 95% or more, 96% or more, 97% or more, 98% or more, or 99% or more. Here, the method for measuring the inkjet droplet parameter may include the steps of: ejecting 500 drops of a first photopolymerizable composition sample onto a substrate via an inkjet device, and then setting the average spacing between the formed droplets to B1 (unit: μm); setting the average spacing between droplets of another second photopolymerizable composition sample, which has been left in an inkjet head for 3 days at a temperature of 40°C or less, to B2 (unit: μm) in the same manner as the first photopolymerizable composition sample; and calculating the inkjet droplet parameter according to the following formula 2. Specifically, when the inkjet droplet parameter (IDP) of the photopolymerizable composition satisfies the above numerical range, ink can be ejected smoothly from the inkjet head without ink clogging. Furthermore, the inkjet droplet parameters of the photopolymerizable composition may be factors that affect one or more of the refractive index, haze value, and light transmittance of the cured film.
[0163] [Formula 2]
[0164] JPEG2026516319000024.jpg16170
[0165] According to another aspect of the present invention, an optical component can be provided that includes a cured film obtained by curing the photopolymerizable composition. Specifically, the haze of the cured film may be 3% or less, 2% or less, or less than 1.0%, and the average transmittance in the wavelength range of 380 to 720 nm may be 95% or more, 96% or more, or 97% or more.
[0166] For example, the optical component may be an optical film or a patterned film.
[0167] According to yet another embodiment of the present invention, the cured film may be placed on a substrate. For example, the substrate may be a silicon wafer or the like.
[0168] In another example, the optical component can be manufactured by applying the photopolymerizable composition of the above embodiment onto the substrate using a Mayer bar, a coating applicator, or an inkjet device, and then exposing it to light curing using an LED lamp or a metal halide lamp. At this time, the photopolymerizable composition may be applied in a single-film form and then photocured to form an optical component in the form of a general optical film, or, if necessary, it may be applied using the inkjet device to have a certain pattern form and then photocured. In this case, the optical component may be in the form of a patterned film on the substrate, in which a cured film patterned in a polyhedral form such as a prism structure is formed.
[0169] The optical components described above, such as optical films or pattern films, may have a general thickness depending on their type and the structure of the electronic element to which they are applied, and for example, they may have a thickness that can be adjusted within the range of 0.01 μm to 1000 μm.
[0170] In some cases, the refractive index of the cured film, measured at a wavelength of 450 nm using an ellipsometer, may be 1.60 or higher.
[0171] 3. Electronic elements
[0172] According to yet another aspect of the present invention, an electronic element including the optical member is provided.
[0173] According to yet another aspect of the present invention, an electronic element is provided comprising a cured film obtained by curing a photopolymerizable composition of several embodiments. For example, the electronic element may be an organic light-emitting element, a solar cell element, an electrochromic material, an electrophoretic element, an organic thin-film transistor, or an organic memory element.
[0174] According to yet another embodiment of the present invention, the cured film obtained by curing the photopolymerizable composition may be placed on the front surface of the electronic element, specifically, to seal the front surface of the electronic element. Specifically, by sealing the front surface of the electronic element with the cured film, the refractive index can be increased while satisfying physical properties equivalent to those of existing elements, thereby improving the light efficiency of the electronic element (e.g., OLED).
[0175] The following describes embodiments of the present invention in detail so that those with ordinary skill in the art to which the present invention pertains can easily implement it. However, these are merely examples, and the scope of the present invention is not limited to the following.
[0176] [Example of manufacturing preparation: Preparation of monomers, initiators, and surfactants]
[0177] surface tension
[0178] The surface tensions of the monomers shown in Table 1 below were measured at a temperature of 25°C using a surface tension meter (device name: KRUSS K20) with either the Du Nouy Ring Method or the Wilhelmy Plate Method.
[0179] Liquid refractive index
[0180] The liquid refractive indices of the monomers shown in Table 1 below were measured at 25°C using a KEM RA-620 measuring instrument.
[0181] viscosity
[0182] The viscosity of the monomers shown in Table 1 below was measured at 25°C using a Brookfleld DV2T.
[0183] [Table 1]
[0184] [C6-4]
[0185] JPEG2026516319000026.jpg26170
[0186] In addition, initiators and surfactants were prepared as shown in Table 2 below.
[0187] [Table 2]
[0188] [Manufacturing example: Production of photopolymerizable compositions]
[0189] Photopolymerizable compositions were prepared using the compositions and content (in parts by weight) listed in Tables 3 and 4 below.
[0190] [Table 3] TIFF2026516319000029.tif180165
[0191] [Table 4]
[0192] [Table 5] TIFF2026516319000032.tif246157TIFF2026516319000033.tif137170
[0193] [Experimental Example: Evaluation of Physical Properties of Monomers, Photopolymerizable Compositions, and Optical Films]
[0194] 1) Deviation of surface tension between monomers
[0195] The surface tension of the monomers used in the production of each photopolymerizable composition in the above examples and comparative examples was measured at 25°C using a surface tension meter (device name: K20, KRUSS) with the Du Nouy Ring or Wilhelmy Plate method, and the deviation of the second monomer relative to the first monomer was calculated. Specifically, the deviation of surface tension between monomers was calculated using the following formula 1.
[0196] [Formula 1]
[0197] The difference in surface tension between monomers = |Surface tension of the first monomer - Surface tension of the second monomer|
[0198] Evaluation Criteria
[0199] ◎: When the difference in surface tension between monomers is 5.0 mN / m or less.
[0200] O: When the difference in surface tension between monomers is greater than 5.0 mN / m and less than or equal to 8.0 mN / m.
[0201] X: When the difference in surface tension between monomers exceeds 8.0 mN / m
[0202] 2) Purity
[0203] The purity of the monomers used in the production of each photopolymerizable composition in the above examples and comparative examples was measured using liquid chromatography (apparatus: Waters ACQUITY UPLC I-Class / ACQUITY UPLC BEH Shield RP18 Column) or gas chromatography (apparatus: Agilnet / PerkinElmer HP7890B / DB-625 Column).
[0204] Evaluation Criteria
[0205] ◎: When the purity is 98% or higher
[0206] O: When the purity is between 96% and 98%.
[0207] △: When the purity is between 94% and 96%
[0208] X: If the purity is less than 94%
[0209] 3) Viscosity (absolute viscosity)
[0210] The absolute viscosity of each photopolymerizable composition in the above examples and comparative examples was measured at a temperature of 25°C using a viscometer (device name: Brookfield Viscometer).
[0211] Evaluation Criteria
[0212] O: When the viscosity is 5-40 cP at 25℃
[0213] X: When the viscosity at 25℃ falls outside the range of 5-40 cP.
[0214] 4) Surface tension
[0215] The surface tension of the photopolymerizable compositions in each of the above examples and comparative examples was measured at 25°C using a surface tension meter (device name: KRUSS K20) by the Du Nouy Ring or Wilhelmy Plate method.
[0216] Evaluation Criteria
[0217] O: When the surface tension of the photopolymerizable composition is 20-60 mN / m
[0218] X: When the surface tension of the photopolymerizable composition falls outside the range of 20-60 mN / m.
[0219] 5) Refractive index
[0220] After coating each of the above-mentioned examples and comparative examples with a photopolymerizable composition onto a silicon wafer, a 1,500 mJ / cm² load was applied for 10 seconds. 2A cured film (optical film) with a thickness of 2 μm was formed by irradiating with UV light at a specified dose. The refractive index (at a wavelength of 450 nm) of the cured film was measured using an ellipsometer.
[0221] Evaluation Criteria
[0222] O: When the refractive index measurement of the single film is 1.60 or higher.
[0223] △: When the refractive index measurement of the single film is between 1.58 and less than 1.60
[0224] X: When the refractive index measurement of the single film is less than 1.58
[0225] 6) Transparency
[0226] The average transmittance at wavelengths (380-780 nm) of the cured film, which was formed in the same manner as the refractive index measurement method described above, was measured using a UV-vis spectrometer (device name: Agilent Cary4000).
[0227] Evaluation Criteria
[0228] O: When the average transmittance value is 97% or higher
[0229] △: When the average transmittance value is between 95% and 97%.
[0230] X: When the average transmittance value is less than 95%
[0231] 7) Hayes
[0232] To measure the haze of the cured film manufactured using the same method as described above for refractive index, a haze meter (COH400 from NIPPON DENSHOKU Co., Ltd.) was used.
[0233] Evaluation Criteria
[0234] ◎: When the haze measurement is less than 1.0%
[0235] O: When the haze measurement is between 1.0% and 3.0%
[0236] X: If the haze measurement exceeds 3.0%
[0237] 8) Inkjet ejection characteristics (A1, A2)
[0238] When the photopolymerizable compositions of each of the above examples and comparative examples were ejected using an inkjet device (Unijet's OmniJet Series) equipped with a head (product name: KM1024i-SHE, Konica Minolta) that ejects droplets quantified to 6 picoliters, the droplets ejected to a distance of 3 mm or less from the nozzle surface were photographed with a CCD camera, and the angle of deviation from the nozzle was confirmed to measure the first inkjet ejection characteristic (A1). Here, A1 is defined as a parameter (unit: °) indicating the straightness of the droplet ejected during the initial inkjet ejection.
[0239] Thereafter, the photopolymerizable composition was left in the Inkjet Head for 3 days at a temperature of 40°C or less, and then the second inkjet ejection characteristic (A2) was measured in the same manner as the first inkjet ejection characteristic (A1). Here, A2 is defined as a parameter (unit: °) indicating the straightness of droplets ejected during continuous ejection or inkjet ejection after a long waiting period.
[0240] Evaluation Criteria
[0241] ◎: When the inkjet ejection characteristics A1 and A2 values are 0.1° or less for the entire nozzle.
[0242] O: When the inkjet ejection characteristics A1 and A2 values are greater than 0.1° and less than or equal to 0.3° for the entire nozzle.
[0243] △: When the inkjet ejection characteristics A1 and A2 values are 0.3° or less for 50% of the total nozzles.
[0244] X: When the inkjet ejection characteristics A1 and A2 values exceed 0.3° for the entire nozzle.
[0245] 9) Inkjet Droplet Parameter (IDP)
[0246] The photopolymerizable compositions of the above examples and comparative examples were dispensed as 500 drops onto a substrate using an inkjet device (Unijet OmniJet Series) equipped with a head (product name: Konica Minolta KM1024i-SHE) that dispenses droplets quantified to 6 picoliters. The average spacing between the formed droplets was then measured using an optical microscope to evaluate the first inkjet droplet characteristics (B1).
[0247] Subsequently, the photopolymerizable composition, which had been left in an inkjet head for 3 days at a temperature of 40°C or less, was evaluated for its second inkjet droplet characteristics (B2) using the same method as described above for the first inkjet droplet characteristics. Then, the IDP was calculated using the following formula 2. Here, the units for B1 and B2 are μm.
[0248] [Formula 2]
[0249] JPEG2026516319000034.jpg16170
[0250] Evaluation Criteria
[0251] O: When the Inkjet Droplet Parameter (IDP) value is 99% or higher
[0252] △: When the Inkjet Droplet Parameter (IDP) value is between 95% and 99%
[0253] X: If the Inkjet Droplet Parameter (IDP) value is less than 95%
[0254] On the other hand, Figure 2 shows the results of inkjet droplet parameters for the photopolymerizable compositions in the examples and comparative examples. Referring to Figure 2, it can be confirmed that the examples exhibit superior inkjet droplet characteristics compared to the comparative examples.
[0255] [Table 6] TIFF2026516319000036.tif189170
[0256] [Table 7]
[0257] [Table 8] TIFF2026516319000039.tif124170
[0258] Although preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art that utilize the basic concepts of the present invention as defined in the following claims also fall within the scope of the present invention.
Claims
1. A first monomer having a first photocurable functional group; A second monomer having a second photocurable functional group; and Initiator; The first and second monomers satisfy the following formula 1: Photopolymerizable composition: [Formula 1] C=|A-B|≦8.0mN / m In the above formula 1, C is the absolute value (mN / m) of the deviation of the surface tension of the second monomer from 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.
2. The surface tension of the first monomer is 43 mN / m or less. The photopolymerizable composition according to claim 1.
3. The first monomer includes a structure represented by the following chemical formula 1, The photopolymerizable composition according to claim 1: 【Chemistry 1】 In the aforementioned chemical formula 1, A comprises one or more structures: a substituted or unsubstituted aryl group; a substituted or unsubstituted aromatic heterocycle; and a substituted or unsubstituted bicyclic ring. X 1 This is a directly bonded, or a divalent linking group having 1 to 20 carbon atoms, which may or may not contain one or more oxygen atoms. X 2 This is a directly bonded, or a divalent linking group having 1 to 20 carbon atoms, which may or may not contain one or more oxygen atoms. R is the first photocurable functional group.
4. In the aforementioned chemical formula 1, A is a substituted or unsubstituted aryl group having 6 to 14 carbon atoms. X 1 This is a direct bond, X 2 This is a divalent linking group having 1 to 10 carbon atoms, which may or may not contain one or more oxygen atoms. The photopolymerizable composition according to claim 3.
5. The first monomer is It contains one or more compounds selected from the group consisting of benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxybenzyl (meth)acrylate, O-phenylphenoxyethyl (meth)acrylate, biphenyl (meth)acrylate, biphenylethyl (meth)acrylate, and compounds represented by the following chemical formulas 2 to 9. The photopolymerizable composition according to claim 1: 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 In the aforementioned 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 an independent integer between 0 and 10.
6. The purity of the first monomer is 95% or higher. The photopolymerizable composition according to claim 1.
7. The purity of the first monomer is 98% or higher. The photopolymerizable composition according to claim 1.
8. The content of the first monomer is, The amount is 30 to 90 parts by weight per 100 parts by weight of the total monomer including the first monomer and the second monomer. The photopolymerizable composition according to claim 1.
9. The preceding second monomer is The structure includes the structure represented by the following chemical formula 10, The photopolymerizable composition according to claim 1: 【Chemistry 10】 In the aforementioned chemical formula 10, B and B' comprise the same or different second photocurable functional groups, Y contains one or more oxygen atoms, and includes a substituted or unsubstituted hydrocarbon structure with 4 to 50 carbon atoms. n and m are integers between 0 and 2. The condition satisfies n + m = 1 or 2.
10. In the aforementioned chemical formula 10, Y is an aliphatic or aromatic structure with 4 to 50 carbon atoms. Containing an alkylene oxide with 6 or more carbon atoms, an alkylene group with 6 or more carbon atoms, or an alkenylene group with 6 or more carbon atoms, The photopolymerizable composition according to claim 9.
11. The preceding second monomer is It contains one or more compounds 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 di(meth)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 compounds represented by the following chemical formula 11. The photopolymerizable composition according to claim 1: 【Chemistry 11】 In the aforementioned chemical formula 11, Each R is independently either hydrogen or an alkyl group. a, b, and c are integers such that a + b + c = 1 to 20.
12. In the aforementioned chemical formula 11, b is 0, and a and c are integers between 1 and 20. The photopolymerizable composition according to claim 11.
13. The content of the initiator is The amount is 0.5 to 10 parts by weight per 100 parts by weight of the total monomer including the first monomer and the second monomer. The photopolymerizable composition according to claim 1.
14. The initiator includes a radical initiator. The photopolymerizable composition according to claim 1.
15. It further comprises one or more selected from the group consisting of surfactants, amine enhancers, and photosensitizers. The photopolymerizable composition according to claim 1.
16. The content of the aforementioned surfactant is The amount is 0.001 to 20 parts by weight per 100 parts by weight of the total monomer including the first monomer and the second monomer. The photopolymerizable composition according to claim 15.
17. The photopolymerizable composition according to claim 1, which is in a solvent-free form.
18. The absolute viscosity measured at 25°C is 5–40 cP. The photopolymerizable composition according to claim 1.
19. An electronic element comprising a cured film obtained by curing the photopolymerizable composition according to claim 1.