Curable composition, cured film thereof, and optical member and display device comprising same

Abstract

The present invention provides a curable composition comprising a monofunctional polymeric first monomer, a bifunctional polymeric second monomer, and a trifunctional or greater polymeric third monomer, wherein, other than a polymeric group comprising a (meth)acryloyloxy group, the first monomer, second monomer, and third monomer consist solely of hydrocarbon groups and contain no heteroatoms.

Description

Curable composition, cured film thereof, and optical member and display device including the same

[0001] The present invention relates to a curable composition, a cured film thereof, and an optical member and a display device comprising the same.

[0002] The application of encapsulating materials is essential for organic semiconductor devices to block external moisture and oxygen and to protect the device from mechanical and physical shocks. Furthermore, even with encapsulation, there are issues regarding performance and lifespan degradation caused by external moisture and oxygen, or by outgases generated from the outside or inside.

[0003] To address this, methods such as applying a photocurable sealant to the substrate, attaching a hygroscopic agent, or applying glass raw materials (frit) have been proposed. However, while these methods are applicable to small-area devices for mobile products, they are difficult to apply to large-area or flexible devices.

[0004] Recently, multilayer thin film encapsulation methods that encapsulate both organic and inorganic layers together are being developed or applied. In this method, the organic and inorganic layers protect the device through mutually complementary roles. To achieve this, the organic layer must have excellent adhesion to the inorganic layer, low outgassing, and ensure light transmittance characteristics for front-facing light emission. Furthermore, for application in large-area or flexible devices, the organic layer must be able to be formed using inkjet printing. Since inkjet printing requires ensuring ejection capabilities from the inkjet head, the organic layer material is required to have low viscosity characteristics.

[0005] In addition, regarding touch panels, electrical noise generated in the components can increase touch malfunctions as the panel becomes thinner, so low dielectric properties of the organic layer are also required.

[0006] The present invention aims to provide a curable composition having excellent low dielectric constant characteristics and modulus, comprising monomers composed solely of hydrocarbon groups excluding polymerization groups, a curable film thereof, and an optical member and a display device comprising the same.

[0007] The above tasks and additional tasks are described in detail below.

[0008] In order to solve the aforementioned problem,

[0009] In one embodiment, the present invention provides a curable composition comprising a monofunctional polymerizable first monomer, a difunctional polymerizable second monomer, and a trifunctional or more polymerizable third monomer, wherein the first monomer, the second monomer, and the third monomer consist only of hydrocarbon groups except for a polymerizing group comprising a (meth)acryloyloxy group, and are free of heteroelements.

[0010] In addition, the present invention provides, in one embodiment, a cured film comprising a cured product of the curable composition.

[0011] In addition, the present invention provides an optical member comprising the hardened film in one embodiment.

[0012] In addition, the present invention provides, in one embodiment, a display device comprising the cured film as a sealing material.

[0013] A curable composition according to one embodiment of the present invention comprises monomers consisting only of hydrocarbon groups excluding polymerization groups, and can realize a curable film, an optical member, and a display device having excellent low dielectric constant characteristics and modulus.

[0014] The above effects and additional effects are described in detail below.

[0015] Before describing the present invention in detail below, it should be understood that the terms used in this specification are intended only to describe specific embodiments and are not intended to limit the scope of the invention, which is defined solely by the appended claims. Unless otherwise stated, all technical and scientific terms used in this specification have the same meaning as generally understood by those skilled in the art.

[0016] Throughout this specification and claims, unless otherwise noted, the terms "comprise," "comprising," and "comprising" mean including the mentioned article, step, or group of articles and steps, and are not used to mean excluding any other article, step, or group of articles or groups of steps.

[0017] Throughout this specification and claims, the term “aryl” means comprising an aromatic hydrocarbon ring group having C5-50, e.g., phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, perylenyl, crisenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzocrisenyl, anthracenyl, stilbenyl, pyrenyl, etc., and “heteroaryl” means an aromatic ring having C2-50 comprising at least one heteroatom, e.g., pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, It may mean including heterocyclic rings formed from acrridinyl, phenanthrolinyl, thienyl, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acrridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzofuran ring, thiazole ring, thiadiazole ring, benzothiophene ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ring, etc. Additionally, the term "arylene" means that a hydrogen in the above aryl group is replaced by a direct bond to become a divalent substituent, and specific examples are not limited to cases where the above-described aryl structure becomes a divalent substituent. Likewise, the term "heteroarylene" means that a hydrogen in the above heteroaryl group is replaced by a direct bond to become a divalent substituent, and specific examples are not limited to cases where the above-described heteroaryl structure becomes a divalent substituent.

[0018] Also, in the chemical formula, Ar x(where x is an integer) means, unless specifically defined, a substituted or unsubstituted C6–C50 aryl group, or a substituted or unsubstituted C2–C50 heteroaryl group, and L x (where x is an integer) means a directly bonded, substituted, or unsubstituted C6–C50 arylene group, or a substituted or unsubstituted C2–C50 heteroarylene group, unless specifically defined, and R x (where x is an integer) means, unless specifically defined, hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C1-C30 sulfide group, substituted or unsubstituted C6-C50 aryl group, or substituted or unsubstituted C2-C50 heteroaryl group.

[0019] Throughout this specification and claims, the term “substituted or unsubstituted” refers to a deuterium, halogen, amino group, cyano group, nitrile group, nitro group, nitroso group, sulfamoyl group, isothiocyanate group, thiocyanate group, carboxyl group, carbonyl group, or a C1–C30 alkyl group, a C1–C30 alkylsulfinyl group, a C1–C30 alkylsulfonyl group, a C1–C30 alkylsulfanyl group, a C1–C12 fluoroalkyl group, a C2–C30 alkenyl group, a C1–C30 alkoxy group, a C1–C12 N-alkylamino group, a C2–C20 N,N-dialkylamino group, a substituted or unsubstituted C1–C30 sulfide group, a C1–C6 N-alkylsulfamoyl group, a C2–C12 N,N-dialkylsulfamoyl group, It may mean that it is substituted or not substituted with one or more groups selected from the group consisting of C0-C30 silyl groups, C3-C20 cycloalkyl groups, C3-C20 heterocycloalkyl groups, C6-C50 aryl groups, and C3-C50 heteroaryl groups. Additionally, throughout this specification, the same symbols may have the same meaning unless specifically stated otherwise.

[0020] Meanwhile, matters described in the specification using the above-defined terms such as "aryl," "heteroaryl," "arylene," "heteroarylene," and "substitution" are deemed to include the examples listed above and their combinations; accordingly, the above-mentioned terms may be replaced by the examples listed above or subsequently modified.

[0021] In addition, when ranges such as "C2 to C50" or "0 to 7" are described in this specification, they may be reduced to various ranges within the described ranges even without special description, and are deemed to be described in this specification. For example, C2 to C50 is deemed to describe various reduced ranges such as C5 to C50, C6 to C30, C6 to C20, C6 to C15, C6 to C10, and C12 to C30, in addition to C2 to C50. Accordingly, the description of numerical ranges in this specification may be reduced and corrected later.

[0022] Meanwhile, various embodiments of the present invention may be combined with any other embodiments unless explicitly stated otherwise. Hereinafter, embodiments of the present invention and the effects thereof will be described.

[0023] A curable composition according to one embodiment of the present invention comprises a monofunctional polymerizable first monomer, a difunctional polymerizable second monomer, and a trifunctional or more polymerizable third monomer, wherein the first monomer, the second monomer, and the third monomer consist only of hydrocarbon groups except for polymerization groups and do not contain heteroelements. Specifically, the polymerization groups may include (meth)acryloyloxy groups.

[0024] A curable composition according to one embodiment of the present invention consists entirely of hydrocarbon groups, excluding polymerization groups, and contains no heteroatoms, thereby significantly lowering the dielectric constant. Therefore, when used as an encapsulating material for a display device, it can prevent malfunctions of touch panels, etc.

[0025] According to one embodiment of the present invention, the monofunctional polymerizable monomer may be represented by the following chemical formula 1 and may include one or more types.

[0026] <Chemical Formula 1>

[0027]

[0028] In the above chemical formula 1,

[0029] The above R1 is hydrogen or a C1-C10 alkyl group, and

[0030] The above R2 is a linear or branched C1-C30 alkylene group.

[0031] According to one embodiment of the present invention, in Formula 1, R2 may specifically be a linear or branched C1-C25, C2-C25, C3-C25, C5-C25, C5-C20, or C8-C20 alkylene group. More specifically, R2 may be a linear or branched C10-C20 alkylene group. Within the above range, low dielectric constant and modulus properties may be excellent.

[0032] In addition, according to one embodiment of the present invention, the second monomer may be represented by the following chemical formula 2 and may include one or more types.

[0033] <Chemical Formula 2>

[0034]

[0035] In the above chemical formula 2,

[0036] The above R1 is each independently hydrogen or a C1-C10 alkyl group, and

[0037] The above R3 is a linear or branched C1-C50 alkylene group, and may or may not include a cyclic cycloalkyl group structure.

[0038] Specifically, the above R3 may be a linear or branched alkylene group of C5~C50, C8~C50, C10~C50, C5~C43, C8~C43, C10~C43, C15~C43, C20~C43, C23~C43, C15~C40, C15~C35, or C20~C35. Within the above range, low dielectric constant and modulus properties may be excellent.

[0039] In addition, according to one embodiment of the present invention, the second monomer may be represented by the following chemical formula 2-1 or chemical formula 2-2, and may include one or more types.

[0040] <Chemical Formula 2-1>

[0041]

[0042] <Chemical Formula 2-2>

[0043]

[0044] In the above chemical formulas 2-1 and 2-2,

[0045] The above R1 is each independently hydrogen or a C1-C10 alkyl group, and

[0046] The above a, b, c, and d are each independently integers from 0 to 32, and

[0047] a+b+c+d is within the range of 20 to 40.

[0048] According to one embodiment of the present invention, in Formula 2-1 and Formula 2-2, a, b, c, and d may each independently be within the range of 1 to 15, and more specifically, within the range of 5 to 10. Additionally, a+b+c+d may specifically be within the range of 20 to 35. Within the above ranges, low dielectric constant and modulus characteristics may be excellent.

[0049] According to one embodiment of the present invention, in the formulas 2-1 and 2-2, the ratio of a+c to b+d may be 1:0.1 to 0.1:1, specifically 1:0.5 to 0.5:1, 1:0.6 to 0.6:1, 1:0.7 to 0.7:1, 1:0.8 to 0.8:1, or 1:0.9 to 0.9:1. More specifically, the ratio of a+c to b+d may be 1:1.

[0050] In addition, according to one embodiment of the present invention, the third monomer may be represented by the following chemical formula 3 and may include one or more types.

[0051] <Chemical Formula 3>

[0052]

[0053] In the above chemical formula 3,

[0054] The above R1 is each independently hydrogen or a C1-C10 alkyl group, and

[0055] The above R4 is a linear or branched C1-C50 trivalent alkyl group, and may or may not include a cyclic cycloalkyl group structure.

[0056] Specifically, the above R4 may be a linear or branched trivalent alkyl group of C3~C40, C5~C40, C10~C40, C5~C33, C8~C33, C10~C33, C15~C33, C20~C33, C23~C33, C15~C30, C15~C25, or C5~C25. Within the above range, low dielectric constant and modulus properties may be excellent.

[0057] In addition, according to one embodiment of the present invention, the third monomer may be represented by the following chemical formula 3-1 or chemical formula 3-2, and may include one or more types.

[0058] <Chemical Formula 3-1>

[0059]

[0060] <Chemical Formula 3-2>

[0061]

[0062] The above R1 is each independently hydrogen or a C1-C10 alkyl group, and

[0063] The above a, b, c, and d are each independently integers from 0 to 32, specifically within the range of 1 to 10, and

[0064] a+b+c+d is within the range of 1 to 11.

[0065] According to one embodiment of the present invention, in the formulas 3-1 and 3-2, a+b+c+d may be within the range of 3 to 8. Within this range, low dielectric constant and modulus characteristics may be excellent.

[0066] A curable composition according to one embodiment of the present invention may include 50 to 65 parts by weight of the first monomer, 15 to 25 parts by weight of the second monomer, and 5 to 10 parts by weight of the third monomer. Within the above range, low dielectric constant and modulus characteristics may be excellent.

[0067] In addition, the weight ratio of the first monomer and the second monomer may be 1:0.15 to 1:0.60. In addition, the weight ratio of the first monomer and the third monomer may be 1:0.10 to 1:0.25. In addition, the weight ratio of the second monomer and the third monomer may be 1:0.2 to 1:0.6. Within the above ranges, low dielectric constant and modulus characteristics may be excellent, and viscosity more suitable for inkjet printing may be obtained.

[0068] Meanwhile, the curable composition according to one embodiment of the present invention may further include an oligomer or polymer composed solely of hydrocarbons. This allows for even better low dielectric constant and modulus properties.

[0069] Specifically, the oligomer or polymer composed solely of the above hydrocarbon may include one or more compounds represented by the following chemical formula 4.

[0070] <Chemical Formula 4>

[0071]

[0072] In the above chemical formula 4,

[0073] x is an integer from 1 to 20, and n is an integer from 1 to 20, and

[0074] x+n is an integer from 2 to 40, and specifically can be an integer from 2 to 20.

[0075] According to one embodiment of the present invention, the oligomer or polymer composed solely of the hydrocarbon may be included in an amount of 1 to 10 parts by weight, specifically 3 to 7 parts by weight, based on a total weight of 100 parts by weight of the monomers. Within this range, the low dielectric constant and modulus properties may be superior.

[0076] Meanwhile, a curable composition according to one embodiment of the present invention may include a photopolymerization initiator. The photopolymerization initiator may include at least one of a phosphine oxide-based compound, an acetophenone-based compound, an acylphosphine oxide-based compound, (E)-2-(acetoxyimino)-1-(9,9-diethyl-9H-fluorene-2-yl)butanone, [1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazoyl-3-yl]-1-(O-acetyloxime), an oxime-based compound, and an oxime ester-based compound. Specifically, the photopolymerization initiator may include at least a phosphine oxide-based compound. When using the aforementioned types of photopolymerization initiators, stable photocuring of the curable composition can be induced, thereby improving the optical properties of the cured product of the curable composition. As the above photopolymerization initiator, for example, phosphine oxide-based compound Irgacure 819, acetophenone-based compounds Irgacure 369 and Irgacure 907, acylphosphine oxide-based compound Darocure TPO, oxime-based compound OXE-01, and oxime ester-based compound OXE-04 may be used.

[0077] Meanwhile, the curable composition according to one embodiment of the present invention may optionally include a photosensitizer and may be used in conjunction with a photopolymerization initiator. Specific examples of the photosensitizer include thioxanthone series such as ITX (2-isopropylthioxanthone) and DETX (2,4-diethylthioxanthone), and quinone series such as CQ (camphorquinone), BQ (benzilquinone), and DMQ (9,10-dimethylanthraquinone), but are not limited thereto.

[0078] According to one embodiment of the present invention, with respect to 100 parts by weight of the monomer mixture, the content of the photopolymerization initiator may be 1 part by weight or more and 20 parts by weight or less, 5 parts by weight or more and 15 parts by weight or less, 5 parts by weight or more and 10 parts by weight or less, 10 parts by weight or more and 20 parts by weight or less, 10 parts by weight or more and 15 parts by weight or less, or 15 parts by weight or more and 20 parts by weight or less. By controlling the content of the photopolymerization initiator to the aforementioned range, the polymerization reaction can be carried out effectively and stably. When a photosensitizer is used in combination, its content may be 0.1 parts by weight or more and 2.0 parts by weight or less, 0.1 parts by weight or more and 1.5 parts by weight or less, 0.1 parts by weight or more and 1.0 parts by weight or less, 0.2 parts by weight or more and 2.0 parts by weight or less, 0.2 parts by weight or more and 1.5 parts by weight or less, or 0.2 parts by weight or more and 1.0 parts by weight or less, relative to 100 parts by weight of the monomer mixture.

[0079] Meanwhile, in addition to the above-mentioned components, the curable composition according to one embodiment of the present invention may optionally use solvents, antioxidants, UV absorbers, thermal polymerization inhibitors, leveling agents, surfactants, lubricants, etc., together, but is not limited to.

[0080] According to one embodiment of the present invention, the viscosity of the curable composition for inkjet may be 5 cP or more and 30 cP or less. The viscosity of the curable composition may be measured at 25°C. The curable composition having a viscosity satisfying the aforementioned range may be easy to use in an inkjet.

[0081] As another embodiment, the present invention provides a cured film comprising a cured product of the aforementioned curable composition, wherein the cured film has a dielectric constant of 2.5 or less and a modulus of 1.1 GPa or more.

[0082] Specifically, the permittivity may be 2.45 or less, and may be in the range of 2.3 to 2.5. The modulus may be 2.0 GPa or more.

[0083] In addition, the cured film according to one embodiment of the present invention may have an outgassing of 80 ppm or less, specifically 50 ppm or less.

[0084] According to one embodiment of the present invention, the cured film exhibits low dielectric constant characteristics while having a modulus within the above range, has excellent mechanical properties, can prevent delamination, and has low outgassing, thereby preventing performance degradation and improving lifespan characteristics.

[0085] One embodiment of the present invention provides an optical member comprising the hardened film.

[0086] According to one embodiment of the present invention, the optical member can achieve excellent optical properties by including the cured film. In addition, the optical member can have excellent stability as discoloration is effectively suppressed even under high temperature and high humidity conditions.

[0087] According to one embodiment of the present invention, the optical member may include a substrate; and the cured film provided on the substrate. Additionally, the cured film may be formed by photocuring after the curable composition is applied to the substrate by an inkjet process. In this case, a well-known substrate, such as bare glass, may be used as the substrate.

[0088] In addition, the optical member may be manufactured by applying the curable composition onto the substrate using a Mayer bar, a coating applicator, or an inkjet device, and then proceeding with photocuring by exposing it to light using, for example, an LED lamp or a metal halide lamp in an air atmosphere. At this time, the curable composition may be applied in a single film form and then photocured to form an optical member in the form of a general optical film, but if necessary, it may also be applied using the inkjet device to form a specific pattern and then photocured. In this case, the optical member may take the form of a pattern film in which a cured film patterned in a polyhedral shape, for example, such as a prism structure, is formed on the substrate.

[0089] One embodiment of the present invention provides a display device comprising the cured film as an organic encapsulation member. The cured film may be included in a multilayer thin film encapsulation member and may follow conventional configurations well known in the art; therefore, further description thereof is omitted.

[0090] Hereinafter, the present invention will be described in detail with reference to examples to specifically explain the invention. However, the embodiments according to the present invention may be modified in various different forms, and the scope of the present invention is not to be interpreted as being limited to the embodiments described below. The embodiments of this specification are provided to more completely explain the present invention to those with average knowledge in the art.

[0091] First monomer

[0092] The following compounds were prepared as the first monomer.

[0093]

[0094] Second monomer

[0095] The following compounds were prepared as second monomers.

[0096]

[0097] Third monomer

[0098] The following compounds were prepared as third monomers.

[0099]

[0100] Oligomers or polymers composed solely of hydrocarbons

[0101] The following compounds were prepared as oligomers or polymers composed solely of hydrocarbons.

[0102]

[0103] Photopolymerization initiators and photosensitizers

[0104] 3 parts by weight of Irgacure 819 as a photopolymerization initiator and 0.3 parts by weight of ITX (2-Isopropyl thioxanthone) as a photosensitizer were used together.

[0105] Examples 1 to 6

[0106] Preparation of a curable composition

[0107] A curable composition was prepared by mixing and stirring the components according to the composition and content of Table 4 below. The content in Table 4 below refers to parts by weight.

[0108] Preparation of hardened film

[0109] Using an inkjet device (UniJet, OmniJet), the curable composition prepared above was applied onto a bare glass substrate to form a single film with a thickness of 10 μm.

[0110] Subsequently, using a 395nm LED curing machine, 2J / cm 2 A cured film (thickness: 10 μm) containing a cured product of an inkjet curable composition was prepared by irradiating a single film with UV light.

[0111] Classification 1st Monomer 2nd Monomer 3rd Monomer Polymer Photoinitiator Photosensitizer Type Content Type Content Type Content Type Content Content Example 1 A-162.3 B-122.8 C-16.6 D-153.00.3 Example 2 A-166 B-124.1 C-16.6 D-03.00.3 Example 3 A-262.3 B-122.8 C-16.6 D-153.00.3 Example 4 A-162.3 B-222.8 C-16.6 D-153.00.3 Example 5A-362.3B-122.8C-16.6D-153.00.3 Example 6A-162.3B-322.8C-26.6D-153.00.3 Comparative Example 1A-462.3B-122.8C-16.6D-153.00.3 Comparative Example 2A-162.3B-422.8C-16.6D-153.00.3 Comparative Example 3A-162.3B-122.8C-36.6D-153.00.3 Comparative Example 4A-562. 3B-122.8C-16.6D-153.00.3 Comparative Example 5A-662.3B-122.8C-16.6D-153.00.3 Comparative Example 6A-162.3B-522.8C-16.6D-153.00.3 Comparative Example 7A-162.3B-622.8C-16.6D-153.00.3 Comparative Example 8A-162.3B-722.8C-16.6D-153.00.3 Comparative Example 9A-162.3B-122.8C- 46.6D-153.00.3 Comparative Example 10A-150.1B-135C-16.6D-153.00.3 Comparative Example 11A-175B-110.1C-16.6D-153.00.3 Comparative Example 12A-167.1B-124.6-0D-153.00.3 Comparative Example 13A-156.2B-120.5C-115D-153.00.3 Comparative Example 14A-162.3B-122.8C-16.6D-253.00.3

[0112] Comparative Examples 1 to 14

[0113] Preparation of a curable composition

[0114] The same procedure as in Example 1 was followed, but a compound was prepared with the components and content of Table 4, mixed, and stirred to produce a curable composition.

[0115] Preparation of hardened film

[0116] The same procedure as in Example 1 was followed, but a curable film was prepared using the curable composition prepared in each comparative example.

[0117] Experimental Example

[0118] The following experiments were conducted on the curable compositions and cured films prepared in Examples 1 to 6 and Comparative Examples 1 to 14, and the results are listed in Table 6 below, and the comprehensive evaluation is listed in Table 7.

[0119] 1. Viscosity

[0120] The viscosity of the compositions prepared in the examples and comparative examples was measured at 25°C using a Brookfield LVT viscometer.

[0121] 2. Outgas

[0122] The compositions prepared in the examples and comparative examples were coated onto bare glass to a thickness of 10 μm using a spin coater, and then cured by irradiating with a 395 nm UV LED at 2000 mW / cm². The prepared glass was cut into 1 cm x 6 cm pieces, and out-gas was analyzed using a Purge & Trap GC / Mass (JAI). Detailed analysis conditions are shown in Table 5. The measured out-gas results were determined as follows.

[0123] Out-gas 50ppm or less: ◎

[0124] Out-gas 51 ~ 80ppm : ○

[0125] Out-gas 81ppm or higher: X

[0126] Classification Details Collection Conditions Purge & Trap temperature 90 ℃ Purge & Trap time 30 min Cold Trap Temperature -30 ℃ Sample size 1 cm x 6 cm Desorption flow 50 ml / min Column type HP-5 MS Inside diameter 0.25 mm Length 60 m Film thickness 0.25 ㎛ GC / MS condition method 40℃(3 min) -10℃ / min -160℃(7 min) -15℃ / min -280℃(25 min) Flow 1 ml / min Split ratio 1 / 30

[0127] 3. Permittivity

[0128] The dielectric constant was measured as follows.

[0129] The compositions prepared in the examples and comparative examples were coated onto a bottom electrode (low-resistance wafer) to a thickness of approximately 8 μm using a spin coater, and a coating film was fabricated using a 395 nm UV LED. A metal mask with an electrode size of 3 mm x 3 mm was placed over the fabricated coating film, and a top electrode (Pt) was coated using a sputter. A frequency of 1 kHz to 1 MHz was applied to the formed top and bottom electrodes, and the change in capacitance was measured. (Agilent Semiconductor Device Analyzer, B1500A) To measure the dielectric constant, the actual thickness of the coating film was measured using an SEM. The dielectric constant measured at 100 kHz was determined as follows.

[0130] Decision

[0131] Permittivity 2.45 or less: ◎

[0132] Permittivity 2.46~2.50 : ○

[0133] Permittivity 2.51 or higher: X

[0134] 4. Modulus

[0135] The modulus was measured as follows.

[0136] The compositions prepared in the examples and comparative examples were coated onto a wafer to a thickness of approximately 8 μm using a spin coater, and then a coating film was prepared using a 395 nm UV LED. The modulus of the prepared coating film was measured using a Nanoindenter. The measured results were determined as follows.

[0137] Decision

[0138] Modulus 2.0 GPa or higher : ◎

[0139] Modulus 1.1 ~ 1.9GPa : ○

[0140] Modulus 1.0 GPa or less : X

[0141] Classification Viscosity Dielectric Constant Durability (Modulus) Out-gas Example 1 24.0 2.4 0 2.0 47.0 Example 2 22.0 2.5 0 1.9 51.0 Example 3 25.6 2.4 9 1.8 55.0 Example 4 19.8 2.5 0 2.1 49.0 Example 5 20.9 2.4 31.4 53.0 Example 6 23.4 2.4 12.1 50.0 Comparative Example 1 23.7 3.5 0 2.3 61.0 Comparative Example 2 23.9 3.3 6 2.6 63.0 Comparative Example 3 24.5 2.6 42.4 66.0 Comparative Example 4 17.3 3.1 03 .37 1.0 Comparative Example 5 26.4 2.4 10.5 6 3.0 Comparative Example 6 22.1 2.6 12.1 5 7.0 Comparative Example 7 23.4 2.5 32.2 5 9.0 Comparative Example 8 26.7 2.4 6 0.9 6 2.0 Comparative Example 9 25.1 2.4 5 0.9 6 1.0 Comparative Example 10 26.0 2.5 32.5 6 8.0 Comparative Example 11 22.0 2.3 9 0.8 8 4.0 Comparative Example 12 22.7 2.4 4 0.6 9 8.0 Comparative Example 13 25.2 2.7 12.6 5 6.0 Comparative Example 14 23.9 2.5 22.2 7 1.0

[0142] Classification Dielectric Constant Durability (Modulus) Out-gas Example 1 ◎◎◎ Example 2 ○○○ Example 3 ○○○ Example 4 ○◎◎ Example 5 ◎○○ Example 6 ◎◎◎ Comparative Example 1 X◎○ Comparative Example 2 X◎○ Comparative Example 3 X◎○ Comparative Example 4 X◎○ Comparative Example 5 ◎X○ Comparative Example 6 X◎○ Comparative Example 7 X◎○ Comparative Example 8 ○X○ Comparative Example 9 ◎X○ Comparative Example 10 X◎○ Comparative Example 11 ◎XX Comparative Example 12 ◎XX Comparative Example 13 X◎○ Comparative Example 14 X◎X

[0143] As can be seen from the results of Tables 6 and 7 above,

[0144] It can be confirmed that the curable composition according to one embodiment of the present invention exhibits significantly superior viscosity, low dielectric constant, durability, and outgassing characteristics compared to the curable composition of the comparative example.

[0145] Specifically, in the case of Comparative Examples 1 to 3, where a portion of the monomer contains a heteroatom, the dielectric constant is high and is unsuitable for low dielectric applications, and

[0146] In the case of Comparative Examples 4 and 5, the structure of the first monomer deviates from the specific embodiments of the present invention, resulting in low dielectric constant or reduced durability, and

[0147] In the case of Comparative Examples 6 to 8, the structure of the second monomer deviates from the specific embodiments of the present invention, resulting in low dielectric constant or reduced durability, and

[0148] In the case of Comparative Example 9, the structure of the third monomer deviates from the specific embodiment of the present invention, resulting in reduced durability, and

[0149] In the case of Comparative Example 14, the structure of the polymer deviates from the specific embodiment of the present invention, resulting in reduced dielectric constant and out-gas characteristics, and

[0150] In the case of Comparative Examples 10 to 13, the content of each monomer deviates from the specific embodiments of the present invention, resulting in reduced low dielectric constant, durability, or / and outgassing properties.

[0151] A person skilled in the art can easily grasp and understand the effects of the invention from the descriptions of the above examples and comparative examples and the results in the table, so a detailed explanation is omitted.

Claims

Monofunctional polymerizable first monomer; A difunctional polymerizable second monomer; and Comprising a polymerizable third monomer with three or more functionalities; and A curable composition in which the first monomer, second monomer, and third monomer are composed solely of hydrocarbon groups, except for a polymerization group containing a (meth)acryloyloxy group, and no heteroelements are present. In paragraph 1, The above monofunctional polymerizable monomer is a curable composition represented by the following chemical formula 1: <Chemical Formula 1> In the above chemical formula 1, The above R1 is hydrogen or a C1-C10 alkyl group, and The above R2 is a linear or branched C1-C30 alkylene group. In paragraph 1, The above second monomer is a curable composition represented by the following chemical formula 2: <Chemical Formula 2> In the above chemical formula 2, The above R1 is each independently hydrogen or a C1-C10 alkyl group, and The above R3 is a linear or branched C1-C50 alkylene group, and may or may not include a cyclic cycloalkyl group structure. In paragraph 1, The above second monomer is a curable composition represented by the following chemical formula 2-1 or chemical formula 2-2. <Chemical Formula 2-1> <Chemical Formula 2-2> In the above chemical formulas 2-1 and 2-2, The above R1 is each independently hydrogen or a C1-C10 alkyl group, and The above a, b, c, and d are each independently integers from 0 to 32, and a+b+c+d is within the range of 20 to 40. In paragraph 4, A curable composition in which a, b, c, and d are each independently within the range of 1 to 15. In paragraph 1, The above third monomer is a curable composition represented by the following chemical formula 3. <Chemical Formula 3> In the above chemical formula 3, The above R1 is each independently hydrogen or a C1-C10 alkyl group, and The above R4 is a linear or branched C1-C50 alkyl group, and may or may not include a cyclic cycloalkyl group structure. In paragraph 1, The above third monomer is a curable composition represented by the following chemical formula 3-1 or chemical formula 3-2. <Chemical Formula 3-1> <Chemical Formula 3-2> In the above chemical formulas 3-1 and 3-2, The above R1 is each independently hydrogen or a C1-C10 alkyl group, and The above a, b, c, and d are each independently integers from 0 to 32, and a+b+c+d is within the range of 1 to 11. In Paragraph 7, A curable composition in which a, b, c, and d are each independently within the range of 1 to 10. In paragraph 1, A curable composition comprising 50 to 65 parts by weight of the first monomer, 15 to 25 parts by weight of the second monomer, and 5 to 10 parts by weight of the third monomer. In paragraph 1, A curable composition further comprising an oligomer or polymer composed solely of hydrocarbons. In Paragraph 10, The oligomer or polymer composed solely of the above hydrocarbons is a curable composition represented by the following chemical formula 4. <Chemical Formula 4> In the above chemical formula 4, x is an integer from 1 to 20, and n is an integer from 1 to 20, and x+n is an integer from 2 to 40. In Paragraph 10, A curable composition comprising 1 to 10 parts by weight of an oligomer or polymer composed solely of the above hydrocarbons, based on 100 parts by weight of the total monomers. In paragraph 1, A curable composition in which the weight ratio of the first monomer and the second monomer is 1:0.15 to 1:0.

60. In paragraph 1, A curable composition in which the weight ratio of the first monomer and the third monomer is 1:0.10 to 1:0.

25. In paragraph 1, A curable composition in which the weight ratio of the second monomer and the third monomer is 1:0.2 to 1:0.

6. A cured film comprising a cured product of the curable composition of claim 1, A hardened film having a permittivity of 2.5 or less and a modulus of 1.1 GPa or more. An optical member comprising a hardened film according to paragraph 16. A display device comprising a cured film according to Clause 16 as an organic encapsulation member.

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