polymer

Abstract

The present application may provide a polymer, a crosslinkable composition containing the same, a method for manufacturing the crosslinkable composition, and uses of the polymer or crosslinkable composition. The present application may provide a polymer and crosslinkable composition that can form a material with excellent antistatic function, a method for manufacturing the same, and uses thereof. The present application may provide a polymer and crosslinkable composition that can exhibit antistatic function without the addition of a separate antistatic agent, that does not bleed out components that exhibit the antistatic function, that is easy to store, and that can stably maintain the performance of an adhesive after being applied to the adhesive, as well as a method for manufacturing the same and uses thereof.

Description

[Technical Field]

[0001] (Cross-reference to related applications) This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0133526 dated October 17, 2022, the entire contents of the documents of which are incorporated herein by reference.

[0002] (Technical field) The present application relates to a polymer, a crosslinkable composition comprising the same, a method for producing said polymer, and uses of said polymer or crosslinkable composition. [Background technology]

[0003] Antistatic materials can be applied in a variety of fields. For example, materials with antistatic properties and adhesive or cohesive properties are used in optical devices such as LCDs (Liquid Crystal Displays) and OLEDs (Organic Light Emitting Diodes).

[0004] An LCD includes a liquid crystal panel having a liquid crystal layer and a polarizer, and an antistatic adhesive may be used to attach the liquid crystal panel and the polarizer. An OLED device may also use an antistatic adhesive for an OLED panel.

[0005] A common method for producing materials such as pressure-sensitive adhesives or adhesives with antistatic properties is to mix an antistatic agent with a tacky polymer, such as an acrylic polymer. Various ionic compounds and surfactants are known as usable antistatic agents. However, these antistatic agents can bleed out of the pressure-sensitive adhesive or adhesive during use or storage, causing contamination, or can float, resulting in problems such as bubbles or peeling. Furthermore, the antistatic agent can affect the performance of the pressure-sensitive adhesive or adhesive, particularly reducing the reworkability of the pressure-sensitive adhesive.

[0006] To address these issues, a technique for constructing a pressure-sensitive adhesive or the like by directly polymerizing an antistatic monomer, such as an ionic monomer, with an acrylic polymer is known. In this method, the ionic monomer is immediately added during the polymerization process and polymerization is carried out. However, this method typically results in problems such as the formation of a non-uniform polymer due to the ionic monomer's reduced affinity for the solvent used as the polymerization medium, or the formed polymer being insoluble in the solvent, making storage difficult.

[0007] Therefore, there is a need for a material that can solve the above problems. Summary of the Invention [Problem to be solved by the invention]

[0008] This application relates to a polymer, a crosslinkable composition containing the polymer, a method for producing the crosslinkable composition, and uses of the polymer or crosslinkable composition. It is also an object of this application to provide a polymer and a crosslinkable composition that can form a material with excellent antistatic properties, a method for producing the same, and uses thereof. It is also an object of this application to provide a polymer and a crosslinkable composition that can exhibit antistatic properties without the addition of a separate antistatic agent, that do not bleed out components that exhibit the antistatic properties, that are easy to store, and that can stably maintain the performance of adhesives after being applied to them, as well as a method for producing the same and uses thereof. [Means for solving the problem]

[0009] Of the physical properties referred to in this specification, those that are affected by temperature are those measured at room temperature unless otherwise specified.

[0010] In this specification, the term "room temperature" refers to a natural temperature that is neither heated nor cooled, and means, for example, any temperature within a range of about 10° C. to 30° C., such as a temperature of about 15° C., about 18° C., about 20° C., about 23° C., or about 25° C. Unless otherwise specified in this specification, the unit of temperature is ° C.

[0011] When pressure affects the results of physical properties mentioned in this specification, the properties are measured at normal pressure unless otherwise specified. The term normal pressure refers to natural pressure that is neither pressurized nor reduced, and is usually about 1 atmosphere (about 700 to 800 mmHg).

[0012] When humidity affects the results of any physical property mentioned in this specification, the physical property is measured at room temperature and pressure with unadjusted humidity, unless otherwise specified.

[0013] The present application relates to a polymer. As is well known, the term polymer refers to a substance formed by covalently linking at least two units (such as a monomer or an oligomer). In one example, the polymer refers to a substance having a structure in which the at least two units are covalently linked and having a molecular weight above a certain level.

[0014] The polymer may be an acrylic polymer, the term acrylic polymer meaning a polymer that contains as a major component polymerized units of acrylic monomers.

[0015] The polymerized unit in the above means a unit formed by the monomer being contained in the polymer in a state where the monomer forms a covalent bond by polymerization.

[0016] In this specification, the acrylic monomer means (meth)acrylic acid or a derivative thereof (for example, an alkyl acrylate or an alkyl methacrylate).

[0017] As used herein, the term (meth)acrylic means acrylic or methacrylic, or both.

[0018] In the above, the polymer containing the polymerized units of the acrylic monomer as a main component means that the proportion of the polymerized units of the acrylic monomer is 50 wt % or more, 55 wt % or more, 60 wt % or more, 65 wt % or more, 70 wt % or more, 75 wt % or more, 80 wt % or more, 85 wt % or more, 90 wt % or more, or 95 wt % or more, but 100 wt % or less, based on the total weight of all polymerized units present in the polymer.

[0019] In one example, the polymer may be an ionic polymer that includes ionic moieties.

[0020] In one example, the polymer may include alkyl(meth)acrylate units, which are polymerized units formed by polymerization of the alkyl(meth)acrylate.

[0021] In the present application, the alkyl(meth)acrylate may be, for example, an alkyl(meth)acrylate in which the number of carbon atoms in the alkyl group is within the range of 1 to 20, 1 to 16, 1 to 12, 4 to 12, or 4 to 8. The alkyl group of the alkyl(meth)acrylate may be linear, branched, or cyclic.

[0022] Specific examples of the alkyl (meth)acrylate include, but are not limited to, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, t-butyl (meth)acrylate, sec-butyl (meth)acrylate, pentyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, 2-ethylbutyl (meth)acrylate, isononyl (meth)acrylate, n-octyl (meth)acrylate, and isooctyl (meth)acrylate.

[0023] The weight ratio of the alkyl (meth)acrylate units to the weight of all polymerized units contained in the polymer may be adjusted, and the weight ratio may be 30% by weight or more, 31% by weight or more, 33% by weight or more, 34% by weight or more, 35% by weight or more, 36% by weight or more, 37% by weight or more, 38% by weight or more, 39% by weight or more, 40% by weight or more, 41% by weight or more, 42% by weight or more, 43% by weight or more, 44% by weight or more, 45% by weight or more, 46% by weight or more, 47% by weight or more, 48% by weight or more, 49% by weight or more, 50% by weight or more, 51% by weight or more, 52% by weight or more, 53% by weight or more, 54% by weight or more, 55% by weight or more, 56% by weight or more, or the like. It may be 57% by weight or more or 58% by weight or more, or may be 80% by weight or less, 79% by weight or less, 78% by weight or less, 77% by weight or less, 76% by weight or less, 75% by weight or less, 74% by weight or less, 73% by weight or less, 72% by weight or less, 71% by weight or less, 70% by weight or less, 69% by weight or less, 68% by weight or less, 67% by weight or less, 66% by weight or less, 65% by weight or less, 64% by weight or less, 63% by weight or less, 62% by weight or less, 61% by weight or less, 60% by weight or less, or 59% by weight or less. The weight ratio may be within a range between any of the above-mentioned lower limits and any of the above-mentioned upper limits.

[0024] The polymer may further include a unit of the following Chemical Formula 1 in addition to the alkyl (meth)acrylate unit.

[0025] (chemical formula 1) [ka]

[0026] In Chemical Formula 1, L may be an alkylene group or an alkylidene group, R may be a hydrogen atom or an alkyl group, and R1 to R3 may each independently be an alkyl group.

[0027] As used herein, the term "alkylene group" refers to a divalent radical formed by removing one hydrogen atom from each of two different carbon atoms of an alkane. The alkylene group may have 2 to 20, 2 to 16, 2 to 12, 2 to 8, or 2 to 4 carbon atoms. The alkylene group may be linear, branched, or cyclic. The alkylene group may be optionally substituted with at least one substituent.

[0028] As used herein, the term "alkylidene group" refers to a divalent radical formed by removing two hydrogen atoms from one carbon atom of an alkane. The alkylidene group may have 1 to 20, 1 to 16, 1 to 12, 1 to 8, or 1 to 4 carbon atoms. The alkylidene group may be linear, branched, or cyclic. The alkylidene group may be optionally substituted with at least one substituent.

[0029] In Chemical Formula 1, the alkylidene group or alkylene group may be any of the alkylidene groups or alkylene groups described above.

[0030] In Chemical Formula 1, the alkyl group of R may be an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, or may be a methyl group. The alkyl group may be linear, branched, or cyclic. The alkyl group may be optionally substituted with at least one substituent.

[0031] In Chemical Formula 1, R1 to R3 may each independently represent an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, or may be a methyl group or an ethyl group. The alkyl group may be linear, branched, or cyclic. The alkyl group may be optionally substituted with at least one substituent.

[0032] In one example, any one of R1 to R3 in Chemical Formula 1 may be an ethyl group and the remaining two may be methyl groups, or R1 to R3 may all be ethyl groups.

[0033] By introducing such a structure, the polymer can be made to exhibit physical properties suitable for forming an adhesive while ensuring the desired antistatic function.

[0034] The polymer of the present application may contain 20 parts by weight or more, 25 parts by weight or more, 30 parts by weight or more, 35 parts by weight or more, 40 parts by weight or more, 45 parts by weight or more, 50 parts by weight or more, 55 parts by weight or more, or 60 parts by weight or more of the units of Chemical Formula 1 per 100 parts by weight of the alkyl (meth)acrylate units. The polymer of the present application may contain 120 parts by weight or less, 115 parts by weight or less, 110 parts by weight or less, 105 parts by weight or less, 100 parts by weight or less, 95 parts by weight or less, 90 parts by weight or less, 85 parts by weight or less, 80 parts by weight or less, 75 parts by weight or less, 70 parts by weight or less, 65 parts by weight or less, or 60 parts by weight or less of the units of Chemical Formula 1 per 100 parts by weight of the alkyl (meth)acrylate units. The proportion of the units of Chemical Formula 1 may be within the range between any of the lower limits mentioned above and any of the upper limits mentioned above. Within this range, a polymer exhibiting suitable antistatic properties and suitable for forming an adhesive may be provided. A pressure-sensitive adhesive formed from such a polymer exhibits appropriate adhesiveness and antistatic properties, does not cause static electricity contamination, and does not leave contamination on the adherend when removed, and can also ensure stable removability.

[0035] The polymer may contain other polymerized units necessary in addition to the polymerized units.

[0036] For example, the polymer may include units of Formula 2:

[0037] (Chemical formula 2) [ka]

[0038] In Formula 2, L1 may be an alkylene group or an alkylidene group, and R 12 may be a hydrogen atom or an alkyl group, and R 10 and R 11 may each independently be an alkyl group.

[0039] In Chemical Formula 2, the alkylene group may be an alkylene group having 2 to 20, 2 to 16, 2 to 12, 2 to 8, or 2 to 4 carbon atoms. The alkylene group may be linear, branched, or cyclic. The alkylene group may be optionally substituted with at least one substituent.

[0040] In Chemical Formula 2, the alkylidene group may be an alkylidene group having 1 to 20, 1 to 16, 1 to 12, 1 to 8, or 1 to 4 carbon atoms. The alkylidene group may be linear, branched, or cyclic. The alkylidene group may be optionally substituted with at least one substituent.

[0041] In Chemical Formula 2, R 12 The alkyl group may be an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, or may be a methyl group. The alkyl group may be linear, branched, or cyclic. The alkyl group may be optionally substituted with at least one substituent.

[0042] In Chemical Formula 2, R 10 and R 11 may each independently be an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, or may be a methyl group or an ethyl group. The alkyl group may be linear, branched, or cyclic. The alkyl group may be optionally substituted with at least one substituent.

[0043] The unit of Chemical Formula 2 is a unit that acts as a precursor of the unit of Chemical Formula 1 in the process of producing the polymer described below, and may be a unit that remains without being converted to Chemical Formula 1 in the conversion process.

[0044] The polymer of the present application may contain 0.1 parts by weight or more, 0.5 parts by weight or more, 1 part by weight or more, 2 parts by weight or more, 3 parts by weight or more, 4 parts by weight or more, 5 parts by weight or more, 5.5 parts by weight or more, 6 parts by weight or more, 7 parts by weight or more, 8 parts by weight or more, 9 parts by weight or more, 10 parts by weight or more, 11 parts by weight or more, 12 parts by weight or more, 13 parts by weight or more, or 14 parts by weight or more of the units of Chemical Formula 2 relative to 100 parts by weight of the alkyl (meth)acrylate units. The polymer of the present application may contain 30 parts by weight or less, 28 parts by weight or less, 26 parts by weight or less, 24 parts by weight or less, 22 parts by weight or less, 20 parts by weight or less, 18 parts by weight or less, 16 parts by weight or less, 14 parts by weight or less, 12 parts by weight or less, or 11 parts by weight or less of the units of Chemical Formula 2 relative to 100 parts by weight of the alkyl (meth)acrylate units. The proportion of units of Chemical Formula 2 may be within a range between any of the lower limits mentioned above and any of the upper limits mentioned above. Within this range, a polymer exhibiting suitable antistatic properties and suitable for forming a pressure-sensitive adhesive can be provided. Pressure-sensitive adhesives formed from such polymers exhibit suitable adhesion and antistatic properties, do not leave static stains or stains on the adherend upon removal, and can stably ensure removability.

[0045] When units of Chemical Formula 2 are included, the ratio (A / B) of the weight (A) of the units of Chemical Formula 1 to the weight (B) of the units of Chemical Formula 2 may be 0.5 or more, 1 or more, 1.5 or more, 2 or more, 2.5 or more, 3 or more, 3.5 or more, 4 or more, 4.5 or more, 5 or more, or 5.5 or more. In other examples, the ratio may be about 20 or less, 19 or less, 18 or less, 17 or less, 16 or less, 15 or less, 14 or less, 13 or less, 12 or less, 11 or less, 10 or less, 9 or less, 8 or less, 7 or less, 6 or less, 5 or less, or 4 or less. The weight ratio A / B may be within a range between any one of the above upper limits and any one of the above lower limits.

[0046] The polymer may optionally contain further polymerized units in addition to the units described above.

[0047] The molecular weight of the polymer may be adjusted within an appropriate range, for example, the weight average molecular weight (Mw) of the polymer may be about 5,000 g / mol or more, 10,000 g / mol or more, 15,000 g / mol or more, 20,000 g / mol or more, 25,000 g / mol or more, 30,000 g / mol or more, 35,000 g / mol or more, 40,000 g / mol or more, 45,000 g / mol or more, 50,000 g / mol or more, 55,000 g / mol or more, or 60,000 g / mol or more. The weight average molecular weight may be about 200,000 g / mol or less, 150,000 g / mol or less, 100,000 g / mol or less, 90,000 g / mol or less, 80,000 g / mol or less, 70,000 g / mol or less, 60,000 g / mol or less, or 50,000 g / mol or less. The molecular weight of the polymer may be within a range between any of the above lower limits and any of the above upper limits.

[0048] For example, the polymer may have a number average molecular weight (Mn) of about 5,000 g / mol or more, 10,000 g / mol or more, 15,000 g / mol or more, 20,000 g / mol or more, or 25,000 g / mol or more, or about 200,000 g / mol or less, 150,000 g / mol or less, 100,000 g / mol or less, 90,000 g / mol or less, 80,000 g / mol or less, 70,000 g / mol or less, 60,000 g / mol or less, 50,000 g / mol or less, 45,000 g / mol or less, 40,000 g / mol or less, 35,000 g / mol or less, 30,000 g / mol or less, or 25,000 g / mol or less. The molecular weight of the polymer can be within a range between any of the aforementioned lower limits and any of the aforementioned upper limits.

[0049] The weight average molecular weight and number average molecular weight are values ​​measured by GPC (Gel Permeation Chromatograph) using polystyrene as a calibration standard sample, and specific measurement methods are described in the Examples.

[0050] The polymer may have a molecular weight distribution, i.e., a ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn), of 1 or more, 1.5 or more, or 2 or more. In other examples, the ratio Mw / Mn may be about 10 or less, 9 or less, 8 or less, 7 or less, 6 or less, 5 or less, 4 or less, 3 or less, or 2 or less. The molecular weight distribution of the polymer may be within a range between any one of the above-mentioned lower limits and any one of the above-mentioned upper limits.

[0051] The present application further relates to a crosslinkable composition. By crosslinkable composition is meant a composition that can be crosslinked. The crosslinkable composition can be crosslinked to form an adhesive, where the term adhesive is as known in the art.

[0052] The crosslinkable composition may contain a crosslinkable polymer and an ionic polymer, and in this case, the ionic polymer may contain any of the polymers described above.

[0053] On the other hand, in the above, the crosslinkable polymer is a polymer that has a crosslinkable functional group (polar functional group) as described below and can participate in a crosslinking reaction.

[0054] The crosslinkable polymer is also a substance formed by linking at least two units (monomers, oligomers, etc.) via a covalent bond.

[0055] The crosslinkable polymer may be an acrylic polymer, the meaning of which is defined above.

[0056] Therefore, the crosslinkable polymer may also contain polymerized units of the acrylic monomer in an amount of 50% by weight or more, 55% by weight or more, 60% by weight or more, 65% by weight or more, 70% by weight or more, 75% by weight or more, 80% by weight or more, 85% by weight or more, 90% by weight or more, or 95% by weight or more, but not more than 100% by weight, based on the total weight of all polymerized units present in the polymer.

[0057] In one example, the polymer may include alkyl(meth)acrylate units, which are polymerized units formed by polymerization of alkyl(meth)acrylate.

[0058] The types of alkyl(meth)acrylates that can be used in this case are as described above for the ionic polymer. Therefore, as the alkyl(meth)acrylate, for example, an alkyl(meth)acrylate having the carbon number of the alkyl group in the range of 1 to 20, 1 to 16, 1 to 12, 4 to 12, or 4 to 8 may be used. The alkyl group of the alkyl(meth)acrylate may be linear, branched, or cyclic.

[0059] In one example, the polymer may contain, as the alkyl(meth)acrylate units, alkyl(meth)acrylate units (first units) having an alkyl group with 1 to 3 carbon atoms and alkyl(meth)acrylate units (second units) having an alkyl group with 4 or more carbon atoms. This allows properties such as glass transition temperature to be adjusted to an appropriate level, efficiently ensuring desired functions (such as antistatic properties), and providing a polymer with properties suitable for use as an adhesive.

[0060] In one example, the first unit, an alkyl (meth)acrylate unit having an alkyl group with 1 to 3 carbon atoms, may be an alkyl methacrylate unit having an alkyl group with 1 to 3 carbon atoms.

[0061] The number of carbon atoms in the alkyl group contained in the alkyl (meth)acrylate unit which is the second unit may be 4 to 20, 4 to 16, 4 to 12, 4 to 8, or 6 to 8. The second unit may also be an alkyl acrylate unit.

[0062] The weight ratio of the alkyl (meth)acrylate units relative to the weight of all polymerized units contained in the crosslinkable polymer may be adjusted to 60% by weight or more, 61% by weight or more, 63% by weight or more, 64% by weight or more, 65% by weight or more, 66% by weight or more, 67% by weight or more, 68% by weight or more, 69% by weight or more, 70% by weight or more, 71% by weight or more, 72% by weight or more, 73% by weight or more, 74% by weight or more, 75% by weight or more, 76% by weight or more, 77% by weight or more, 78% by weight or more, 79% by weight or more, 80% by weight or more, 81% by weight or more, 82% by weight or more, 83% by weight or more, 84% by weight or more, or 85% by weight or more, or about 95% by weight or less, 94% by weight or less, 93% by weight or less, 92% by weight or less, 91% by weight or less, 90% by weight or less, 89% by weight or less, 88% by weight or less, 87% by weight or less, or 86% by weight or less. The weight ratio may be within a range between any of the aforementioned lower limits and any of the aforementioned upper limits.

[0063] Within the polymer, the ratio (A2 / A1) of the weight of the first unit (A1) to the weight of the second unit (A2) may be adjusted. The ratio (A2 / A1) may be 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, or 7 or more. The ratio (A2 / A1) may be about 20 or less, 19 or less, 18 or less, 17 or less, 16 or less, 15 or less, 14 or less, 13 or less, 12 or less, 11 or less, 10 or less, 9 or less, or 8 or less. The ratio (A2 / A1) may be within the range between any of the above-mentioned lower limits and any of the above-mentioned upper limits. This allows properties such as the glass transition temperature to be adjusted to an appropriate level, efficiently ensuring desired functions (e.g., antistatic properties), and obtaining a polymer with properties suitable for use as an adhesive.

[0064] The polymer may contain other polymerized units necessary in addition to the polymerized units.

[0065] For example, the polymer may include units of Formula 3:

[0066] (Chemical formula 3) [ka]

[0067] In Chemical Formula 3, R4, R5, R8, and R9 are each independently a carbon atom or a carbonyl group, R6 is a carbon atom or an oxygen atom, or is absent, and the bond between R4 and R5 and the bond between R8 and R9 may each independently be a single bond or a double bond.

[0068] In Chemical Formula 3, the absence of R6 means that R5 and R9 are directly linked.

[0069] In Chemical Formula 3, when R4, R5, R6, R8, and R9 are carbon atoms, hydrogen atoms may be bonded to the carbon atoms in accordance with the valency of the overall structure of the compound of Chemical Formula 3.

[0070] In one example, R4, R5, R8, and R9 in Chemical Formula 3 are each independently a carbon atom or a carbonyl group, R6 is a carbon atom or is absent, and the bond between R4 and R5 and the bond between R8 and R9 are each independently a single bond or a double bond, but at least one of R4, R5, R8, and R9 may be a carbonyl group.

[0071] In one example, either R4 or R8 in Chemical Formula 3 is a carbon atom and the other is a carbonyl group, R6 is absent, and the bond between R4 and R8 and the bond between R8 and R9 may be a single bond.

[0072] In one example, R4, R5, R8, and R9 in Chemical Formula 3 are each a carbon atom, R6 is absent, and the bond between R4 and R5 and the bond between R8 and R9 may each be a double bond.

[0073] In one example, R4, R5, R8, and R9 in Chemical Formula 3 are each a carbon atom, R6 is absent, and the bond between R4 and R5 and the bond between R8 and R9 may each be a single bond.

[0074] In one example, R4, R5, R8, and R9 in Chemical Formula 3 are each carbon atoms, and the bond between R4 and R5 and the bond between R8 and R9 may each be a single bond.

[0075] In one example, R4, R5, R8, and R9 in Chemical Formula 3 are each a carbon atom, R6 is an oxygen atom, and the bond between R4 and R5 and the bond between R8 and R9 may each be a single bond.

[0076] When units of Chemical Formula 3 are present, the proportion of the units in the crosslinkable polymer may be, for example, 0.5 parts by weight or more, 1 part by weight or more, 2 parts by weight or more, 3 parts by weight or more, 4 parts by weight or more, 5 parts by weight or more, or 6 parts by weight or more, relative to 100 parts by weight of the alkyl (meth)acrylate units. When units of Chemical Formula 3 are present, the proportion of the units may be, for example, 20 parts by weight or less, 19 parts by weight or less, 18 parts by weight or less, 17 parts by weight or less, 16 parts by weight or less, 15 parts by weight or less, 14 parts by weight or less, 13 parts by weight or less, 12 parts by weight or less, 11 parts by weight or less, 10 parts by weight or less, 9 parts by weight or less, 8 parts by weight or less, or 7 parts by weight or less, relative to 100 parts by weight of the alkyl (meth)acrylate units. When units of Chemical Formula 3 are present, the proportion thereof may be within a range between any of the above-mentioned lower limits and any of the above-mentioned upper limits. Such a range is advantageous for forming a pressure-sensitive adhesive that exhibits an appropriate antistatic function, does not induce staining due to static electricity or staining due to peeling, and exhibits appropriate adhesion and removability.

[0077] The crosslinkable polymer may further include a polar group-containing unit, if necessary. Such a unit is necessary to adjust cohesion or to realize a crosslinked structure. The polar group-containing unit refers to a polymerized unit formed from a monomer having a polar group. The polar group-containing unit may be a hydroxy group-containing unit or a carboxy group-containing unit. The use of a hydroxy group-containing unit is particularly advantageous, but is not limited thereto. The carboxy group-containing unit may cause corrosion in electronic devices, optical devices, etc., so it may not be present in the polymer depending on the application of the polymer.

[0078] Examples of hydroxyl-containing monomers capable of forming hydroxyl-containing units include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 2-hydroxypolyethylene glycol (meth)acrylate, and 2-hydroxypolypropylene glycol (meth)acrylate. In the hydroxyalkyl (meth)acrylate, the alkyl group may have about 1 to 20, 1 to 16, 1 to 12, 1 to 8, 2 to 8, 3 to 8, 4 to 8, or 4 to 6 carbon atoms.

[0079] Examples of carboxyl group-containing monomers capable of forming carboxyl group-containing units include (meth)acrylic acid, 2-(meth)acryloyloxyacetic acid, 3-(meth)acryloyloxypropyl acid, 4-(meth)acryloyloxybutyric acid, acrylic acid dimers, itaconic acid, maleic acid and / or maleic anhydride.

[0080] The polar group-containing units may be contained in the polymer at a ratio of 1 part by weight or more, 2 parts by weight or more, 3 parts by weight or more, 4 parts by weight or more, 5 parts by weight or more, 6 parts by weight or more, 7 parts by weight or more, 8 parts by weight or more, 9 parts by weight or more, 10 parts by weight or more, 11 parts by weight or more, 12 parts by weight or more, or 13 parts by weight or more, relative to 100 parts by weight of the alkyl (meth)acrylate units. The polar group-containing units may be contained in the crosslinkable polymer at a ratio of 30 parts by weight or less, 29 parts by weight or less, 28 parts by weight or less, 27 parts by weight or less, 26 parts by weight or less, 25 parts by weight or less, 24 parts by weight or less, 23 parts by weight or less, 22 parts by weight or less, 21 parts by weight or less, 20 parts by weight or less, 19 parts by weight or less, 18 parts by weight or less, 17 parts by weight or less, 16 parts by weight or less, 15 parts by weight or less, 14 parts by weight or less, or 13.5 parts by weight or less, relative to 100 parts by weight of the alkyl (meth)acrylate units. When the polar group-containing unit is present, the proportion thereof may be within a range between any one of the above-mentioned lower limits and any one of the above-mentioned upper limits. Such a range is effective for forming a PSA that exhibits appropriate antistatic function, does not leave stains on the adherend due to static electricity, and has appropriate removability and adhesiveness, without leaving stains on the adherend during the peeling process.

[0081] The crosslinkable polymer may further contain other polymerized units as necessary.

[0082] The molecular weight of the crosslinkable polymer may be adjusted within an appropriate range, for example, the weight average molecular weight (Mw) of the crosslinkable polymer may be about 10,000 g / mol or more, 50,000 g / mol or more, 100,000 g / mol or more, 150,000 g / mol or more, 200,000 g / mol or more, 250,000 g / mol or more, 300,000 g / mol or more, 350,000 g / mol or more, 400,000 g / mol or more, 450,000 g / mol or more, 500,000 g / mol or more, 550,000 g / mol or more, or 600,000 g / mol or more. The weight average molecular weight may be about 2,000,000 g / mol or less, 1,500,000 g / mol or less, 1,000,000 g / mol or less, 900,000 g / mol or less, 800,000 g / mol or less, 700,000 g / mol or less, or 650,000 g / mol or less. The molecular weight of the polymer may be within a range between any of the above lower limits and any of the above upper limits.

[0083] For example, the molecular weight of the polymer can be expressed as the number average molecular weight (Mn). Weight) may be about 5,000 g / mol or more, 10,000 g / mol or more, 15,000 g / mol or more, 20,000 g / mol or more, 25,000 g / mol or more, 30,000 g / mol or more, 35,000 g / mol or more, 40,000 g / mol or more, 45,000 g / mol or more, 50,000 g / mol or more, 55,000 g / mol or more, 60,000 g / mol or more, 65,000 g / mol or more, 70,000 g / mol or more, 75,000 g / mol or more, 80,000 g / mol or more, 85,000 g / mol or more, 90,000 g / mol or more, 95,000 g / mol or more, or 100,000 g / mol or more. The number average molecular weight may be on the order of about 200,000 g / mol or less, 150,000 g / mol or less, or 100,000 g / mol or less, and the molecular weight of the polymer may be within a range between any of the lower limits set forth above and any of the upper limits set forth above.

[0084] The weight average molecular weight and number average molecular weight can be determined in the same manner as for the ionic polymer.

[0085] The polymer may have a molecular weight distribution, i.e., the ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn), of 1 or more, 1.5 or more, 2 or more, 2.5 or more, 3 or more, 3.5 or more, 4 or more, 4.5 or more, 5 or more, 5.5 or more, or 6 or more. In other examples, the ratio Mw / Mn may be about 10 or less, 9.5 or less, 9 or less, 8.5 or less, 8 or less, 7.5 or less, 7 or less, 6.5 or less, or 6 or less. The molecular weight distribution of the crosslinkable polymer may be within a range between any one of the above-mentioned lower limits and any one of the above-mentioned upper limits.

[0086] The crosslinkable composition includes a crosslinkable polymer as described above in combination with the ionic polymer described above.

[0087] In the crosslinkable composition, the proportion of the crosslinkable polymer is not particularly limited, but may be about 50% by weight or more, 55% by weight or more, 60% by weight or more, 65% by weight or more, 70% by weight or more, 75% by weight or more, 80% by weight or more, 85% by weight or more, or 90% by weight or more. In other examples, the proportion may be less than 100% by weight, 95% by weight or less, 90% by weight or less, 85% by weight or less, 80% by weight or less, 75% by weight or less, or 70% by weight or less. The proportion may be within a range between any of the above-mentioned lower limits and any of the above-mentioned upper limits.

[0088] The ionic polymer may be included in an amount of 1 part by weight or more, 2.5 parts by weight or more, 5 parts by weight or more, 10 parts by weight or more, 15 parts by weight or more, 20 parts by weight or more, 25 parts by weight or more, 30 parts by weight or more, 35 parts by weight or more, or 40 parts by weight or more, based on 100 parts by weight of the crosslinkable polymer. The ionic polymer may be included in an amount of 60 parts by weight or less, 55 parts by weight or less, 50 parts by weight or less, 45 parts by weight or less, 40 parts by weight or less, 35 parts by weight or less, 30 parts by weight or less, 25 parts by weight or less, 20 parts by weight or less, 15 parts by weight or less, 10 parts by weight or less, or 7.5 parts by weight or less, based on 100 parts by weight of the crosslinkable polymer. The amount may be within a range between any of the lower limits described above and any of the upper limits described above. A crosslinkable composition with desired properties may be appropriately formed within such an amount.

[0089] The crosslinkable composition, when including the crosslinkable and ionic polymer, may also include various other necessary additives.

[0090] For example, the crosslinkable composition may further include a crosslinking agent, if necessary. When a crosslinking agent is included, at least the crosslinkable polymer in the crosslinkable composition may be present in a crosslinked state. That is, the crosslinking agent may form a crosslinked structure with the crosslinkable polymer including the polar group-containing unit.

[0091] The crosslinking agent may be appropriately selected depending on the type of polar group contained in the crosslinkable polymer. For example, when the polar group is a hydroxy group, an isocyanate crosslinking agent may be typically used as the crosslinking agent. However, the types of applicable crosslinking agents are not limited to the above, and other crosslinking agents may also be appropriately used.

[0092] The isocyanate crosslinking agent may be an aliphatic cyclic polyisocyanate compound and / or an acyclic aliphatic polyisocyanate compound. In the above, "polyisocyanate" means that the compound contains at least two isocyanate groups. The number of isocyanate groups present in the compound may be 2 to 10, 2 to 9, 2 to 8, 2 to 7, 2 to 6, 2 to 5, 2 to 4, or 2 to 3. Examples of the aliphatic cyclic isocyanate compound include isocyanate compounds such as isoborone diisocyanate, methylene dicyclohexyl diisocyanate, and cyclohexane diisocyanate, derivatives such as dimers and trimers thereof, and reaction products of any of the foregoing with polyols (e.g., trimethylolpropane). Examples of the acyclic aliphatic isocyanate compound include alkylene diisocyanate compounds having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, or 1 to 8 carbon atoms, such as hexamethylene diisocyanate, derivatives such as dimers and trimers thereof, and reaction products of any of the foregoing with polyols (e.g., trimethylolpropane), but are not limited thereto.

[0093] The proportion of the crosslinking agent used may be 0.01 parts by weight or more, 0.05 parts by weight or more, 0.1 parts by weight or more, 0.15 parts by weight or more, 0.2 parts by weight or more, or 0.25 parts by weight or more, based on 100 parts by weight of the total of the crosslinkable and ionic polymers (based on solid content). In other examples, the proportion may be approximately 10 parts by weight or less, 9 parts by weight or less, 8 parts by weight or less, 7 parts by weight or less, 6 parts by weight or less, 5 parts by weight or less, 4 parts by weight or less, 3 parts by weight or less, 2 parts by weight or less, 1 part by weight or less, 0.9 parts by weight or less, 0.8 parts by weight or less, 0.7 parts by weight or less, 0.6 parts by weight or less, 0.5 parts by weight or less, 0.4 parts by weight or less, or 0.3 parts by weight or less. The proportion of the crosslinking agent may be within a range between any of the above upper limits and any of the above lower limits.

[0094] Within this range, the crosslinking agent can efficiently form a desired crosslinked structure.

[0095] In consideration of efficient formation of a desired crosslinked structure and stability before crosslinking, the crosslinkable composition may further contain a crosslinking retarder.

[0096] As the crosslinking retarder, known compounds may be used, for example, one or more selected from β-ketoesters such as methyl acetoacetate, ethyl acetoacetate, octyl acetoacetate, oleyl acetoacetate, lauryl acetoacetate and / or stearyl acetoacetate, or β-diketones such as acetylacetone, 2,4-hexanedione and / or benzoylacetone may be used.

[0097] The proportion of the crosslinking retarder used may be 0.1 parts by weight or more, 0.5 parts by weight or more, 1 part by weight or more, 1.5 parts by weight or more, 2 parts by weight or more, 2.5 parts by weight or more, or 3 parts by weight or more, based on 100 parts by weight of the total of the crosslinkable and ionic polymers (based on solid content). In other examples, the proportion may be about 10 parts by weight or less, 9 parts by weight or less, 8 parts by weight or less, 7 parts by weight or less, 6 parts by weight or less, 5 parts by weight or less, 4 parts by weight or less, or 3 parts by weight or less. The proportion of the crosslinking retarder may be within a range between any of the above upper limits and any of the above lower limits.

[0098] To achieve a suitable crosslinking structure, the ratio (A / B) of the weight (A) of the crosslinking retarder to the weight (B) of the crosslinking agent may be about 0.5 or more, 1 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, 9 or more, 10 or more, 11 or more, or 12 or more. The weight ratio (A / B) may be about 30 or less, 28 or less, 26 or less, 24 or less, 22 or less, 20 or less, 18 or less, 16 or less, 14 or less, or 12 or less. The weight ratio A / B may be within a range between any one of the above upper limits and any one of the above lower limits.

[0099] In addition to the above components, the crosslinkable composition may contain other appropriate additive components, such as a silane coupling agent, a tackifier, a multifunctional acrylate, an antifoaming agent, an antioxidant, a surfactant, and / or a plasticizer.

[0100] The present application further relates to a method for producing said crosslinkable composition.

[0101] The method may essentially comprise mixing the crosslinkable polymer and the ionic polymer.

[0102] Each of the polymers may be formed by polymerizing the monomers contained in the mixed monomer mixture in consideration of the desired composition of the polymerized units.

[0103] There is no limitation on the polymerization method, but for example, solution polymerization may be applied.

[0104] When solution polymerization is applied, it is appropriate to carry out at least two reaction stages to obtain the ionic polymer.

[0105] For example, a method for obtaining an ionic polymer containing a unit of Chemical Formula 1 may include the steps of reacting a monomer mixture containing an alkyl(meth)acrylate and a compound of Chemical Formula 4 to obtain a polymer, and reacting the polymer with a haloalkane.

[0106] To incorporate the unit of Chemical Formula 1 into a polymer, one approach is to directly add an ionic monomer containing the structure of Chemical Formula 1 to the monomer mixture for solution polymerization. However, it has been found that such ionic monomers generally have reduced solubility in the solvent used for solution polymerization, resulting in the formation of non-uniform polymers or reduced solubility of the formed polymer in the solvent, which can cause storage problems. Furthermore, ionic polymers formed in this manner are less compatible with the crosslinkable polymer.

[0107] However, the above problem can be solved by preparing a polymer through the two-step reaction using the compound of the following formula 4.

[0108] A compound of the following Chemical Formula 4 may be polymerized to form units of the above Chemical Formula 2, which may then be converted to units of the above Chemical Formula 1 through a reaction with the haloalkane. In this process, by controlling the reaction, some of the units of the above Chemical Formula 2 may be converted to units of the above Chemical Formula 1, while other units may remain.

[0109] (Chemical formula 4) [ka]

[0110] In Formula 4, L1 may be an alkylene group or an alkylidene group, and R 12 may be a hydrogen atom or an alkyl group, and R 10 and R 11 may each independently be an alkyl group.

[0111] An example of the compound of Formula 4 is dialkylaminoalkyl(meth)acrylate.

[0112] In Chemical Formula 4, the alkylene group may be an alkylene group having 2 to 20, 2 to 16, 2 to 12, 2 to 8, or 2 to 4 carbon atoms. The alkylene group may be linear, branched, or cyclic. The alkylene group may be optionally substituted with at least one substituent.

[0113] In Chemical Formula 4, the alkylidene group may be an alkylidene group having 1 to 20, 1 to 16, 1 to 12, 1 to 8, or 1 to 4 carbon atoms. The alkylidene group may be linear, branched, or cyclic. The alkylidene group may be optionally substituted with at least one substituent.

[0114] In Chemical Formula 4, R 12 The alkyl group may be an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, or may be a methyl group. The alkyl group may be linear, branched, or cyclic. The alkyl group may be optionally substituted with at least one substituent.

[0115] In Chemical Formula 4, R 10 and R 11 may each independently be an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, or may be a methyl group or an ethyl group. The alkyl group may be linear, branched, or cyclic. The alkyl group may be optionally substituted with at least one substituent.

[0116] In the method for producing the polymer, the alkyl(meth)acrylate contained in the monomer mixture is a monomer that forms the alkyl(meth)acrylate unit, and the compound of Chemical Formula 4 forms the unit of Chemical Formula 2, which is a precursor for forming the unit of Chemical Formula 1.

[0117] Therefore, the specific type of the alkyl(meth)acrylate in the monomer mixture may be controlled to form the alkyl(meth)acrylate unit, and the ratio of the alkyl(meth)acrylate to the compound of Formula 4 may be the same as that of the alkyl(meth)acrylate unit and the units of Formulas 1 and 2.

[0118] The monomer mixture may further contain a solvent, which may be any solvent commonly used in solution polymerization, such as substituted or unsubstituted aliphatic C1-C olefins such as n-hexane, n-heptane, cyclohexane, and isooctane. 20 One or more solvents selected from saturated hydrocarbon solvents, aliphatic ketone solvents such as acetone, methyl ethyl ketone, methyl propyl ketone, methyl isopropyl ketone, methyl butyl ketone, methyl isobutyl ketone, diethyl ketone, diisopropyl ketone, cyclobutanone, cyclopentanone, and cyclohexanone, aliphatic ester solvents such as methyl acetate, ethyl acetate (EAc), propyl acetate, isopropyl acetate, butyl acetate, and isobutyl acetate, and / or substituted or unsubstituted aromatic solvents such as benzene, toluene, ethylbenzene, and xylene may be used, but the solvents are not limited to these.

[0119] In the polymerization process, the solvent may be included in an amount of 40 parts by weight or more, 45 parts by weight or more, or 50 parts by weight or more, based on 100 parts by weight of the total monomers contained in the monomer mixture. The solvent may be included in an amount of 70 parts by weight or less, 65 parts by weight or less, or 60 parts by weight or less, based on 100 parts by weight of the total monomers. The proportion of the solvent may be adjusted as necessary.

[0120] The monomer mixture may further contain a reaction initiator. The type of the reaction initiator is not particularly limited, and for example, a radical initiator may be used. The radical initiator may be a radical thermal initiator or a radical photoinitiator, and the specific type is not particularly limited.

[0121] For example, the initiator may be an azo-based initiator such as 2,2-azobis-2,4-dimethylvaleronitrile (V-65, manufactured by Wako), 2,2-azobisisobutyronitrile (V-60, manufactured by Wako), and / or 2,2-azobis-2-methylbutyronitrile (V-59, manufactured by Wako), but is not limited thereto.

[0122] The initiator may be present in an appropriate proportion depending on the desired polymer, for example, at a concentration of 200 ppm or more, 250 ppm or more, 300 ppm or more, or 350 ppm or more. In other examples, the initiator may be present at a concentration of 600 ppm or less, 550 ppm or less, 500 ppm or less, or 450 ppm or less.

[0123] The monomer mixture may further include optional additives such as chain transfer agents.

[0124] The method for polymerizing the monomer mixture is not particularly limited, and the polymerization may be carried out by a known solution polymerization method.

[0125] After forming the polymer in the above manner, the polymer may be reacted with a haloalkane to form the unit of Formula 1.

[0126] The reaction may be carried out by adding the haloalkane to a polymerization solution obtained after producing a polymer, or by recovering the polymer from the polymerization solution and then mixing it again with the haloalkane.

[0127] The haloalkane may be a compound in which any hydrogen atom of an alkane is substituted with a halogen, such as, but not limited to, Br, Cl, F, or I.

[0128] The haloalkane may be a haloalkane having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, such as a halomethane or a haloethane. The haloalkane may be linear, branched, or cyclic, and may be optionally substituted with at least one substituent.

[0129] The reaction may be carried out by diluting the haloalkane with an appropriate solvent and mixing it with a polymerization solution containing the polymer or another solution containing the polymer.

[0130] Such reactions may be carried out at temperatures of, for example, about 50° C. or higher, 55° C. or higher, 60° C. or higher, 65° C. or higher, 70° C. or higher, 75° C. or higher, or 80° C. or higher. The reaction temperature may be about 200° C. or lower, 190° C. or lower, 180° C. or lower, 170° C. or lower, 160° C. or lower, 150° C. or lower, 140° C. or lower, 130° C. or lower, 120° C. or lower, 110° C. or lower, 100° C. or lower, 95° C. or lower, 90° C. or lower, 85° C. or lower, or 80° C. The reaction temperature range may be between any of the aforementioned upper limits and any of the aforementioned lower limits.

[0131] The reaction may be carried out for, for example, about 1 hour or more, 5 hours or more, 15 hours or more, or 20 hours or more. The reaction time may be about 200 hours or less, 150 hours or less, 100 hours or less, 90 hours or less, 80 hours or less, 70 hours or less, 60 hours or less, 50 hours or less, 40 hours or less, 30 hours or less, or 20 hours or less. The reaction time may be within a range between any of the above upper limits and any of the above lower limits.

[0132] By the above method, it is possible to obtain a polymer which has a uniform desired monomer composition, has excellent solubility in solvents, and is highly compatible with other polymers such as crosslinkable polymers.

[0133] In the method for producing the crosslinkable composition, the crosslinkable polymer may be produced by applying a known solution polymerization method or the like.

[0134] The method for preparing the crosslinkable composition may further include a step of blending other additives such as the crosslinking retarder and the crosslinking agent.

[0135] The present application further relates to uses of the polymer or crosslinkable composition. The crosslinkable composition or polymer may be used in various fields where, for example, antistatic properties are required.

[0136] For example, the present application relates to a laminate to which the crosslinkable composition or a crosslinked product thereof is applied. In the above, the crosslinked product of the crosslinkable composition may be an adhesive, and in this case, the crosslinkable polymer may be an adhesive polymer.

[0137] Such a laminate may include, for example, an electronic substrate and the pressure-sensitive adhesive attached to one or both sides of the electronic substrate.

[0138] In the above, the type of electronic substrate is not particularly limited, and various types that require antistatic properties may be applied.

[0139] In one example, the electronic substrate may be an OLED (Organic Light Emitting Diode) panel, and in this case, the laminate may be an OLED device including an OLED panel and the adhesive attached to one or both sides of the OLED panel.

[0140] The method for forming the crosslinked product applied to the laminate is not particularly limited. For example, the crosslinked product may be formed by applying an appropriate crosslinking method taking into account the type of polymer and / or crosslinking agent to which the crosslinkable composition is applied. For example, if the polymer and / or crosslinking agent are of a type that is crosslinked by the application of heat, the crosslinked product may be formed by applying appropriate heat, or other crosslinking methods may also be used.

[0141] When the crosslinked product in the laminate is in the form of a layer, the thickness of the layer is not particularly limited and may have an appropriate thickness. For example, it may be 10 μm or more, 30 μm or more, 50 μm or more, 70 μm or more, or 90 μm or more. In other examples, the thickness of the layer may be 500 μm or less, 400 μm or less, 300 μm or less, 200 μm or less, 180 μm or less, 160 μm or less, 140 μm or less, or 120 μm or less. [Effects of the Invention]

[0142] The present application may provide a polymer, a crosslinkable composition containing the same, a method for manufacturing the crosslinkable composition, and uses of the polymer or crosslinkable composition. The present application may provide a polymer and crosslinkable composition that can form a material with excellent antistatic function, a method for manufacturing the same, and uses thereof. The present application may provide a polymer and crosslinkable composition that can exhibit antistatic function without the addition of a separate antistatic agent, that does not bleed out components that exhibit the antistatic function, that is easy to store, and that can stably maintain the performance of an adhesive after being applied to the adhesive, as well as a method for manufacturing the same and uses thereof. [Brief explanation of the drawings]

[0143] [Figure 1] 1 shows the results of NMR analysis of the polymers produced in the production examples. [Figure 2] 1 shows the results of NMR analysis of the polymers produced in the production examples. [Figure 3] 1 shows the results of NMR analysis of the polymers produced in the production examples. [Figure 4]1 shows the results of NMR analysis of the polymers produced in the production examples. DETAILED DESCRIPTION OF THE INVENTION

[0144] The present application will be described in detail through the following examples, but the scope of the present application is not limited to the following examples.

[0145] 1. Analysis methods for polymer structure, components, and component ratios The polymer structure, components, and component ratios were analyzed using HR-MAS (high resolution magic angle spinning) 1H NMR, 1H-13C HSQC (Heteronuclear Single Quantum Coherence) NMR, and 1H-1H COSY (Correlation Spectroscopy) NMR.

[0146] 2. Surface resistance measurement The surface resistance of the pressure-sensitive adhesive layer was measured at a temperature of 25°C and a relative humidity of 40%. The surface resistance was measured using a Mitsubishi Chemical HIRESTA-UP (MCP-HT450) after applying a voltage of 500 V for 10 seconds at the above temperature and relative humidity.

[0147] 3. Evaluation of contamination resistance The stain resistance was evaluated by visually observing the surface condition of the adhesive layer to determine whether staining due to static electricity had occurred on the adhesive layer after measuring the surface resistance.

[0148] The evaluation criteria for the stain resistance are as follows.

[0149] <Evaluation criteria for stain resistance> ◯: No contamination was observed on the surface of the adhesive layer. X: Contamination was observed on the surface of the adhesive layer.

[0150] 4.Reworkability evaluation Reworkability was evaluated by observing the surface state of the adhesive layer after peeling it off after adhering the adhesive layer to the adherend. In the above, a glass substrate was used as the adherend, and peeling was performed at a peeling angle of about 180 degrees and a peeling speed of about 300 mm / min.

[0151] The evaluation criteria for reworkability are as follows.

[0152] <Evaluation Criteria for Reworkability> ○: No residue of the adhesive is confirmed from the surface of the adherend. △: On the surface of the adherend, there is a part of the residue of the adhesive and it is slightly blurred. X: On the surface of the adherend, a large amount of the residue of the adhesive exists and it is blurred.

[0153] 5.GPC (Gel Permeation Chromatograph) The molecular weight was measured using GPC (Gel permeation chromatography). The polymer was put into a 5 mL vial and diluted with THF (tetrahydrofuran) to a concentration of about 1 mg / mL. Then, the calibration standard sample and the sample to be analyzed were filtered through a syringe filter (pore size: 0.45 μm) and then measured. The analysis program used ChemStation of Agilent technologies, and the weight average molecular weight (Mw) and the number average molecular weight (Mn) were obtained by comparing the elution time of the sample with the calibration curve, respectively.

[0154] <GPC Measurement Conditions> Equipment: 1200 series of Agilent technologies Columns: Two PLgel mixed B of Polymer laboratories were used Solvent: THF Column temperature: 35 °C Sample concentration: 1 mg / mL, 200 μL injection Standard sample: Polystyrene (Mp: 3900000, 723000, 316500, 52200, 31400, 7200, 3940, 485)

[0155] Production Example 1. Production of Polymer (A) 2-Ethylhexyl acrylate (EHA), methyl methacrylate (MMA), 2-hydroxyethyl acrylate (HEA), and N-vinyl-2-pyrrolidone (NVP) were added in a weight ratio of 75:10:10:5 (EHA:MMA:HEA:NVP) to a 1-L reactor equipped with a cooling device for easy temperature control and refluxing nitrogen gas. Ethyl acetate (EAc) was added as a solvent. Approximately 50-60 parts by weight of the solvent was added per 100 parts by weight of the total monomers. After purging with nitrogen gas to remove oxygen, the reaction was initiated at 65°C by adding azobisisobutyronitrile (AIBN) as a reaction initiator. The reaction initiator was added at a concentration of approximately 300 ppm.

[0156] The polymerization reaction was carried out for about 5 to 6 hours and was completed when the conversion rate reached about 90% or more, yielding polymer (A).

[0157] The conversion rate is calculated by the following formula 1.

[0158] (Equation 1) Conversion rate (%) = (C / B) / A x 100

[0159] In Equation 1, A is the solid content of the monomer mixture, B is the weight (unit: g) of the polymer after the polymerization reaction before drying, and C is the weight (unit: g) of the polymer after the polymerization reaction after drying.

[0160] In Equation 1, A is the ratio (=W2 / W1) of the weight of the monomer (W2) to the total weight (W1) of the monomer mixture (including the solvent and the monomer), and the weight of the polymer before drying (B) is the weight of the polymer measured after polymerizing the mixture containing the solvent and the monomer.

[0161] The drying for measuring the weight (C) was carried out by holding the polymer at a temperature of about 150° C. for about 30 minutes.

[0162] The polymer (A) had a weight average molecular weight (Mw) of about 600,000 and a number average molecular weight (Mn) of about 100,000.

[0163] Production Example 2: Production of Polymer (B) A 1-L reactor equipped with a cooling device for easy temperature control and refluxing nitrogen gas was charged with butyl acrylate (BA) and 2-(dimethylamino)ethyl acrylate (DMAEA) in a weight ratio of 60:40 (BA:DMAEA), and ethyl acetate (EAc) was added as a solvent to prepare a monomer mixture. Approximately 50-60 parts by weight of the solvent was added per 100 parts by weight of the total monomers. After purging with nitrogen gas to remove oxygen, the polymerization reaction was initiated at 65°C by adding azobisisobutyronitrile (AIBN) as a reaction initiator. The reaction initiator was added at approximately 400 ppm.

[0164] The polymerization reaction was carried out until the conversion rate reached 90% or more to obtain a primary polymer (primary polymer). The conversion rate was determined in the same manner as in Preparation Example 1.

[0165] To the primary polymer, 1 equivalent of bromoethane relative to 2-(dimethylamino)ethyl acrylate (DMAEA) contained in the polymer was added, and the reaction was continued at 80° C. for another 20 hours to obtain the desired polymer (B).

[0166] The weight average molecular weight (Mw) of the obtained polymer (B) was about 50,000, and the number average molecular weight (Mn) was about 25,000.

[0167] 1 and 2 show the NMR analysis results for the primary polymer and polymer (B), where FIG. 1 shows the results for the primary polymer and FIG. 2 shows the results for the final polymer (B).

[0168] 1 and 2, it was confirmed that the 2-(dimethylamino)ethyl acrylate (DMAEA) unit was converted to a unit of the following chemical formula A by the reaction with bromoethane.

[0169] (Chemical formula A) [ka]

[0170] In formula A, R is hydrogen, L is an ethylene group, R1 and R3 are methyl groups, and R2 is an ethyl group.

[0171] Table 1 below shows the weight ratio of the polymerized units contained in the polymer during the manufacturing process, where BA, DMAEA, and Formula A represent the ratios of butyl acrylate, 2-(dimethylamino)ethyl acrylate, and Formula A units, respectively.

[0172] [Table 1]

[0173] Production Example 3: Production of Polymer (C) A 1-L reactor equipped with a cooling device for easy temperature control and refluxing nitrogen gas was charged with butyl acrylate (BA) and 2-(diethylamino)ethyl acrylate (DEAEA) in a weight ratio of 60:40 (BA:DEAEA), and ethyl acetate (EAc) was added as a solvent to prepare a monomer mixture. Approximately 50-60 parts by weight of the solvent was added per 100 parts by weight of the total monomers. After purging with nitrogen gas to remove oxygen, the polymerization reaction was initiated at 65°C by adding azobisisobutyronitrile (AIBN) as a reaction initiator. The reaction initiator was added at approximately 400 ppm.

[0174] The polymerization reaction was carried out until the conversion rate reached 90% or more to obtain a primary polymer (primary polymer). The conversion rate was confirmed in the same manner as in Preparation Example 2.

[0175] To the obtained primary polymer, 1 equivalent of bromoethane relative to the 2-(diethylamino)ethyl acrylate (DEAEA) contained in the polymer was added, and the reaction was continued at 80°C for an additional 20 hours to obtain the desired polymer (C).

[0176] The weight average molecular weight (Mw) of the obtained polymer (C) was about 60,000, and the number average molecular weight (Mn) was about 25,000.

[0177] 3 and 4 show the NMR analysis results for the primary polymer and polymer (C), where FIG. 3 shows the results for the primary polymer and FIG. 4 shows the results for the final polymer (C).

[0178] 3 and 4, it was confirmed that the 2-(diethylamino)ethyl acrylate (DEAEA) unit was converted to a unit of the following chemical formula B by the reaction with bromoethane.

[0179] (Chemical formula B) [ka]

[0180] In chemical formula B, R is hydrogen, L is an ethylene group, and R1 to R3 are ethyl groups.

[0181] Table 2 below shows the weight ratio of the polymerized units contained in the polymer during the manufacturing process, where BA, DMAEA, and Formula B represent the ratios of butyl acrylate, 2-(dimethylamino)ethyl acrylate, and Formula B units, respectively.

[0182] [Table 2]

[0183] Production Example 4: Production of polymer (D) Polymer (D) was prepared in the same manner as in Example 1, except that 2-ethylhexyl acrylate (EHA), 2-hydroxyethyl acrylate (HEA), and N-vinyl-2-pyrrolidone (NVP) were used as monomers in a weight ratio of 85:10:5 (EHA:HEA:NVP).

[0184] Production Example 5: Production of Polymer (E) Polymer (E) was prepared in the same manner as in Example 1, except that 2-ethylhexyl acrylate (EHA), methyl methacrylate (MMA), and 2-hydroxyethyl acrylate (HEA) were used as monomers in a weight ratio of 80:10:10 (EHA:MMA:HEA).

[0185] Example 1 Polymer (A) of Preparation Example 1 and polymer (B) of Preparation Example 2 were mixed in a weight ratio (A:B) of 95:5 to prepare a polymer mixture.

[0186] Next, about 0.25 parts by weight of a crosslinker (DR-7030HD, Sanei Ink) and about 3 parts by weight of acetyl acetone were mixed with 100 parts by weight of the solid content of the polymer mixture, diluted to an appropriate concentration, and mixed uniformly to prepare a pressure-sensitive adhesive composition.

[0187] Next, the pressure-sensitive adhesive composition was coated on a release paper and held at 120° C. for about 4 minutes and 30 seconds to prepare a pressure-sensitive adhesive layer with a thickness of about 100 μm.

[0188] Example 2 A pressure-sensitive adhesive composition and a pressure-sensitive adhesive layer were prepared in the same manner as in Example 1, except that when preparing the polymer mixture, polymer (A) of Preparation Example 1 and polymer (B) of Preparation Example 2 were mixed in a weight ratio (A:B) of 90:10.

[0189] Example 3 A pressure-sensitive adhesive composition and a pressure-sensitive adhesive layer were prepared in the same manner as in Example 1, except that when preparing the polymer mixture, polymer (A) of Preparation Example 1 and polymer (B) of Preparation Example 2 were mixed in a weight ratio (A:B) of 80:20.

[0190] Example 4 A pressure-sensitive adhesive composition and a pressure-sensitive adhesive layer were prepared in the same manner as in Example 1, except that when preparing the polymer mixture, polymer (A) of Preparation Example 1 and polymer (B) of Preparation Example 2 were mixed in a weight ratio (A:B) of 70:30.

[0191] Example 5 A pressure-sensitive adhesive composition and a pressure-sensitive adhesive layer were prepared in the same manner as in Example 1, except that the polymer (C) of Preparation Example 3 was used instead of the polymer (B) of Preparation Example 2.

[0192] Example 6 A pressure-sensitive adhesive composition and a pressure-sensitive adhesive layer were prepared in the same manner as in Example 2, except that the polymer (C) of Preparation Example 3 was used instead of the polymer (B) of Preparation Example 2.

[0193] Example 7 A pressure-sensitive adhesive composition and a pressure-sensitive adhesive layer were prepared in the same manner as in Example 3, except that the polymer (C) of Preparation Example 3 was used instead of the polymer (B) of Preparation Example 2.

[0194] Example 8 A pressure-sensitive adhesive composition and a pressure-sensitive adhesive layer were prepared in the same manner as in Example 4, except that the polymer (C) of Preparation Example 3 was used instead of the polymer (B) of Preparation Example 2.

[0195] Comparative Example 1 Approximately 3 parts by weight of FeAA (Ferric Acetyl Acetonate) and approximately 0.25 parts by weight of an isocyanate compound (DR-7030HD, San-ei Ink) were blended with 100 parts by weight of the polymer (A) of Preparation Example 1, and approximately 0.05 parts by weight of an antistatic agent (Lithium Bis(Trifluoromethanesulfonyl)imide) was further blended with 100 parts by weight of the polymer (A). The mixture was diluted to an appropriate concentration and then uniformly mixed to prepare a pressure-sensitive adhesive composition.

[0196] Next, the pressure-sensitive adhesive composition was coated on a release paper and subjected to a crosslinking reaction at a temperature of 120° C. for about 4 minutes and 30 seconds to prepare a pressure-sensitive adhesive layer having a thickness of about 100 μm or less.

[0197] Comparative Example 2 Approximately 3 parts by weight of FeAA (Ferric Acetyl Acetonate) and approximately 0.25 parts by weight of an isocyanate compound (DR-7030HD, San-ei Ink) were blended with 100 parts by weight of the polymer (A) of Preparation Example 1, and approximately 0.15 parts by weight of an antistatic agent (Lithium Bis(Trifluoromethanesulfonyl)imide) was further blended with 100 parts by weight of the polymer (A). The mixture was diluted to an appropriate concentration and then uniformly mixed to prepare a pressure-sensitive adhesive composition.

[0198] Next, the pressure-sensitive adhesive composition was coated on a release paper and subjected to a crosslinking reaction at a temperature of 120° C. for about 4 minutes and 30 seconds to prepare a pressure-sensitive adhesive layer having a thickness of about 100 μm or less.

[0199] Comparative Example 3 A pressure-sensitive adhesive composition and a pressure-sensitive adhesive layer were prepared in the same manner as in Comparative Example 1, except that the polymer (D) of Preparation Example 4 was used instead of the polymer (A) of Preparation Example 1.

[0200] Comparative Example 4 A pressure-sensitive adhesive composition and a pressure-sensitive adhesive layer were prepared in the same manner as in Comparative Example 2, except that the polymer (D) of Preparation Example 4 was used instead of the polymer (A) of Preparation Example 1.

[0201] Comparative Example 5 A pressure-sensitive adhesive composition and a pressure-sensitive adhesive layer were prepared in the same manner as in Comparative Example 1, except that the polymer (E) of Preparation Example 5 was used instead of the polymer (A) of Preparation Example 1.

[0202] Comparative Example 6 A pressure-sensitive adhesive composition and a pressure-sensitive adhesive layer were prepared in the same manner as in Comparative Example 2, except that the polymer (E) of Preparation Example 5 was used instead of the polymer (A) of Preparation Example 1.

[0203] The evaluation results for the Examples and Comparative Examples are summarized in Tables 3 and 4 below.

[0204] [Table 3]

[0205] [Table 4]

[0206] It can be seen from Table 3 that the PSA composition according to the present application exhibits suitable surface resistance, stain resistance, and reworkability. In particular, it can be seen that when the polymer of Preparation Example 3 is included, more suitable surface resistance is exhibited.

[0207] (Addendum) (Appendix 1) A polymer comprising alkyl(meth)acrylate units and units of the following Chemical Formula 1, wherein the polymer comprises 20 parts by weight or more of the units of Chemical Formula 1 per 100 parts by weight of the alkyl(meth)acrylate units: (chemical formula 1) [ka] (In the above chemical formula 1, L is an alkylene group or an alkylidene group, R is a hydrogen atom or an alkyl group, and R1 to R3 are alkyl groups.)

[0208] (Appendix 2) Attachment 1: The polymer according to claim 1, comprising the alkyl (meth)acrylate unit in a proportion of 30 to 80% by weight.

[0209] (Appendix 3) 2. The polymer of claim 1, further comprising a unit of formula 2: (Chemical formula 2) [ka] (In the above Chemical Formula 2, L1 is an alkylene group or an alkylidene group, and R 12 is a hydrogen atom or an alkyl group, and R 10 and R 11 are each independently an alkyl group.

[0210] (Appendix 4) Attachment 3: The polymer according to Appendix 3, comprising the unit of Chemical Formula 2 in an amount of 0.1 to 30 parts by weight per 100 parts by weight of alkyl (meth)acrylate units.

[0211] (Appendix 5) 4. The polymer according to claim 3, wherein the ratio (A / B) of the weight (A) of the units of the chemical formula 1 to the weight (B) of the units of the chemical formula 2 is within the range of 0.5 to 20.

[0212] (Appendix 6) 2. The polymer of claim 1, having a weight average molecular weight of 200,000 g / mol or less.

[0213] (Appendix 7) a crosslinkable polymer; A crosslinkable composition comprising the polymer of claim 1 as an ionic polymer.

[0214] (Appendix 8) 8. The crosslinkable composition according to claim 7, comprising 1 to 60 parts by weight of the ionic polymer relative to 100 parts by weight of the crosslinkable polymer.

[0215] (Appendix 9) 8. The crosslinkable composition according to claim 7, wherein the crosslinkable polymer comprises the alkyl(meth)acrylate unit.

[0216] (Appendix 10) 10. The crosslinkable composition according to claim 9, wherein the crosslinkable polymer further comprises a unit of the following chemical formula 3: (Chemical formula 3) [ka] (In Chemical Formula 3, R4, R5, R8, and R9 are each independently a carbon atom or a carbonyl group; R6 is a carbon atom, an oxygen atom, or is absent; and the bond between R4 and R5 and the bond between R8 and R9 are each independently a single bond or a double bond.)

[0217] (Appendix 11) Appendix 10: A crosslinkable composition according to Chemical Formula 3, wherein R4, R5, R8, and R9 are each independently a carbon atom or a carbonyl group, R6 is a carbon atom or is absent, and the bond between R4 and R5 and the bond between R8 and R9 are each independently a single bond or a double bond, but at least one of R4, R5, R8, and R9 is a carbonyl group.

[0218] (Appendix 12) 11. The crosslinkable composition according to claim 10, wherein the crosslinkable polymer contains 0.5 to 20 parts by weight of the unit of Chemical Formula 3 relative to 100 parts by weight of alkyl(meth)acrylate units.

[0219] (Appendix 13) 10. The crosslinkable composition of claim 9, wherein the crosslinkable polymer further comprises a polar group-containing unit.

[0220] (Appendix 14) 14. The crosslinkable composition according to claim 13, wherein the crosslinkable polymer contains 1 to 30 parts by weight of the polar group-containing unit relative to 100 parts by weight of the alkyl(meth)acrylate unit.

[0221] (Appendix 15) 8. The crosslinkable composition of claim 7, further comprising a crosslinking agent and a crosslinking retarder.

[0222] (Appendix 16) The crosslinkable composition according to Appendix 15, wherein the crosslinking agent is contained in an amount of 0.01 to 10 parts by weight relative to 100 parts by weight of the total of the crosslinkable and ionic polymers, the crosslinking retarder is contained in an amount of 0.1 to 10 parts by weight relative to 100 parts by weight of the crosslinkable and ionic polymers, and the ratio (A / B) of the weight (A) of the crosslinking retarder to the weight (B) of the crosslinking agent is within a range of 0.5 to 30.

[0223] (Appendix 17) 10. A method for producing a crosslinkable composition according to claim 7, comprising: mixing a crosslinkable polymer and an ionic polymer; The ionic polymer is Reacting a monomer mixture containing alkyl(meth)acrylate and a compound of Formula 4 to obtain a polymer; A method for producing a crosslinkable composition comprising the step of reacting said polymer with a haloalkane. (Chemical formula 4) [ka] (In the above Chemical Formula 4, L1 is an alkylene group or an alkylidene group, and R 12 is a hydrogen atom or an alkyl group, and R 10 and R 11 are each independently an alkyl group.

[0224] (Appendix 18) 18. The method for producing a crosslinkable composition according to claim 17, wherein the reaction of the monomer mixture is a solution polymerization reaction.

[0225] (Appendix 19) An electronic board; A laminate comprising the crosslinkable composition or a crosslinked product thereof according to Appendix 7 attached to one or both surfaces of the electronic substrate.

[0226] (Appendix 20) OLED panel and 10. An OLED device comprising the crosslinkable composition or a crosslinked product thereof according to claim 7 attached to one or both sides of the OLED panel.

Claims

1. A polymer comprising alkyl(meth)acrylate units and units of the following Chemical Formula 1, wherein the units of Chemical Formula 1 are contained in an amount of 20 parts by weight or more per 100 parts by weight of the alkyl(meth)acrylate units: (Chemical formula 1) 【Chemical 1】 (In the above formula 1, L is an alkylene group or an alkylidene group, R is a hydrogen atom or an alkyl group, and R １ ~R ３ is an alkyl group.

2. 2. The polymer according to claim 1, comprising 30 to 80% by weight of said alkyl (meth)acrylate units.

3. The polymer of claim 1 further comprising a unit of Formula 2: (Chemical formula 2) 【Chemistry 2】 (In the above Chemical Formula 2, L １ is an alkylene group or an alkylidene group, and R １２ is a hydrogen atom or an alkyl group, and R １０ and R １１ are each independently an alkyl group.

4. The polymer according to claim 3, comprising the unit of Chemical Formula 2 in an amount of 0.1 to 30 parts by weight per 100 parts by weight of alkyl (meth)acrylate units.

5. 4. The polymer according to claim 3, wherein the ratio (A / B) of the weight (A) of the units of Chemical Formula 1 to the weight (B) of the units of Chemical Formula 2 is in the range of 0.5 to 20.

6. 10. The polymer of claim 1, having a weight average molecular weight of 200,000 g / mol or less.

7. a crosslinkable polymer; A crosslinkable composition comprising the polymer of claim 1 as an ionic polymer.

8. 8. The crosslinkable composition of claim 7, comprising 1 to 60 parts by weight of said ionic polymer per 100 parts by weight of said crosslinkable polymer.

9. The crosslinkable composition of claim 7 , wherein the crosslinkable polymer comprises the alkyl (meth)acrylate units.

10. The crosslinkable composition according to claim 9 , wherein the crosslinkable polymer further comprises a unit of the following formula 3: (Chemical formula 3) 【Chemistry 3】 (In the above-mentioned Chemical Formula 3, R ４ , R ５ , R ８ and R ９ are each independently a carbon atom or a carbonyl group, and R ６ is a carbon atom or an oxygen atom or is absent, and R ４ and R ５ and R ８ and R ９ are each independently a single bond or a double bond.

11. In the above formula 3, R ４ , R ５ , R ８ and R ９ are each independently a carbon atom or a carbonyl group, and R ６ is a carbon atom or is absent, and R ４ and R ５ and R ８ and R ９ are each independently a single bond or a double bond, but R ４ , R ５ , R ８ and R ９ The crosslinkable composition of claim 10, wherein at least one of is a carbonyl group.

12. The crosslinkable composition according to claim 10, wherein the crosslinkable polymer comprises 0.5 to 20 parts by weight of the unit of Chemical Formula 3 per 100 parts by weight of alkyl (meth)acrylate units.

13. The crosslinkable composition of claim 9 , wherein the crosslinkable polymer further comprises a polar group-containing unit.

14. The crosslinkable composition according to claim 13, wherein the crosslinkable polymer contains 1 to 30 parts by weight of the polar group-containing unit per 100 parts by weight of the alkyl (meth)acrylate unit.

15. The crosslinkable composition of claim 7 further comprising a crosslinking agent and a crosslinking retarder.

16. The crosslinkable composition according to claim 15, wherein the crosslinking agent is contained in an amount of 0.01 to 10 parts by weight relative to a total of 100 parts by weight of the crosslinkable and ionic polymers, the crosslinking retarder is contained in an amount of 0.1 to 10 parts by weight relative to a total of 100 parts by weight of the crosslinkable and ionic polymers, and the ratio (A / B) of the weight (A) of the crosslinking retarder to the weight (B) of the crosslinking agent is within a range of 0.5 to 30.

17. A method for producing the crosslinkable composition of claim 7, comprising the steps of: mixing a crosslinkable polymer and an ionic polymer; The ionic polymer is Reacting a monomer mixture containing alkyl(meth)acrylate and a compound of Formula 4 to obtain a polymer; A method for producing a crosslinkable composition comprising the step of reacting said polymer with a haloalkane. (Chemical formula 4) 【Chemistry 4】 (In the above-mentioned Chemical Formula 4, L １ is an alkylene group or an alkylidene group, and R １２ is a hydrogen atom or an alkyl group, and R １０ and R １１ are each independently an alkyl group.

18. The method for producing a crosslinkable composition according to claim 17, wherein the reaction of the monomer mixture is a solution polymerization reaction.

19. An electronic board; A laminate comprising the crosslinkable composition or a crosslinked product thereof according to claim 7 attached to one or both surfaces of the electronic substrate.

20. an OLED panel; An OLED device comprising the crosslinkable composition or a crosslinked product thereof according to claim 7 attached to one or both surfaces of the OLED panel.

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