polymer

Abstract

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

Description

[Technical Field]

[0001] Cross-reference to related applications This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0129930, dated October 11, 2022, the entire contents of which are incorporated herein by reference.

[0002] Technical Field The present application relates to a polymer, an adhesive containing the same, a method for producing the polymer, and uses of the polymer or adhesive. [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 antistatic agents that can be used in this process. However, these antistatic agents can bleed out of the pressure-sensitive adhesive or adhesive during use or storage, causing contamination, or can cause problems such as floating, 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 added immediately 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] The present application relates to a polymer, an adhesive containing the same, a method for producing the polymer, and uses of the polymer or adhesive.

[0009] The present application aims to provide a polymer capable of forming a material with excellent antistatic properties, a manufacturing method thereof, and uses of the polymer. The present application aims to provide a polymer that exhibits antistatic properties without the addition of a separate antistatic agent, that does not bleed out components that exhibit the antistatic properties, 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 manufacturing method thereof and uses of the polymer. [Means for solving the problem]

[0010] Of the physical properties referred to in this specification, those that are affected by temperature are those measured at room temperature unless otherwise specified.

[0011] As used herein, 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.

[0012] When pressure affects the results of physical properties mentioned in this specification, the physical 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 mmHg to 800 mmHg).

[0013] 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.

[0014] 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.

[0015] 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.

[0016] The polymerized unit means a unit formed by the monomer forming a covalent bond through polymerization and being included in the polymer.

[0017] In this specification, the acrylic monomer means (meth)acrylic acid or a derivative thereof (for example, an alkyl acrylate or an alkyl methacrylate).

[0018] As used herein, the term (meth)acrylic means acrylic or methacrylic, or both.

[0019] 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 not more than 100 wt %, based on the total weight of all polymerized units present in the polymer.

[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 moiety 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] 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.

[0024] 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.

[0025] 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.

[0026] The weight ratio of the alkyl (meth)acrylate units to the weight of all polymerized units contained in the polymer may be adjusted. The weight ratio may be 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, or 79% by weight or more, or may be about 90% by weight or less, 89% by weight or less, 88% by weight or less, 87% by weight or less, 86% by weight or less, 85% by weight or less, 84% by weight or less, 83% by weight or less, 82% by weight or less, 81% by weight or less, 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, or 71% 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.

[0027] 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, or 6 or more. The ratio (A2 / A1) may be 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, or 6 or less. The A2 / A1 ratio 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 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.

[0028] The polymer may further include a unit of the following Chemical Formula 1 in addition to the alkyl (meth)acrylate unit.

[0029] [ka]

[0030] 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.

[0031] 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.

[0032] 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.

[0033] In Chemical Formula 1, the alkylidene group or alkylene group may be any of the above alkylidene groups or alkylene groups.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] The polymer of the present application may contain 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, 13 parts by weight or more, or 14 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 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, 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, 7 parts by weight or less, 6 parts by weight or less, or 5 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 a range between any of the above-mentioned lower limits and any of the above-mentioned upper limits. 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.

[0039] The polymer may contain other polymerized units necessary in addition to the above polymerized units.

[0040] For example, the polymer may include units of Formula 2:

[0041] [ka]

[0042] In Chemical Formula 2, 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 are each independently a single bond or a double bond.

[0043] In Chemical Formula 2, the absence of R6 means that R5 and R9 are directly linked.

[0044] In Chemical Formula 2, when R4, R5, R6, R8, and R9 are carbon atoms, hydrogen atoms may be bonded to the carbon atoms in accordance with the valency, taking into account the overall structure of the compound of Chemical Formula 2.

[0045] In one example, R4, R5, R8, and R9 in Chemical Formula 2 are each independently a carbon atom or a carbonyl group, R6 is a single bond or a carbon atom, 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.

[0046] In one example, either R4 or R8 in Chemical Formula 2 is a carbon atom and the other is a carbonyl group, R6 is a single bond, and the bond between R4 and R5 and the bond between R8 and R9 may be a single bond.

[0047] In one example, R4, R5, R8, and R9 in Chemical Formula 2 are each a carbon atom, R6 is a single bond, and the bond between R4 and R5 and the bond between R8 and R9 may each be a double bond.

[0048] In one example, R4, R5, R8, and R9 in Chemical Formula 2 may each be a carbon atom, R6 may be a single bond, and the bond between R4 and R5 and the bond between R8 and R9 may each be a single bond.

[0049] In one example, R4, R5, R6, R8, and R9 in Chemical Formula 2 are each carbon atoms, and the bond between R4 and R5 and the bond between R8 and R9 may each be a single bond.

[0050] In one example, R4, R5, R8, and R9 in Chemical Formula 2 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.

[0051] When units of Chemical Formula 2 are present, the proportion of the units 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, 6 parts by weight or more, or 7 parts by weight or more, relative to 100 parts by weight of the alkyl (meth)acrylate units. When units of Chemical Formula 2 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, 7 parts by weight or less, or 6 parts by weight or less, relative to 100 parts by weight of the alkyl (meth)acrylate units. When units of Chemical Formula 2 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.

[0052] The polymer of the present application may further include a polar group-containing unit, if necessary. Such a unit is necessary to adjust the cohesive strength of the PSA 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. Since a carboxy group-containing unit may cause corrosion in electronic devices, optical devices, etc., the polymer may not be present depending on the application of the polymer.

[0053] Examples of hydroxyl group-containing monomers capable of forming hydroxyl group-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.

[0054] 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.

[0055] 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, 13 parts by weight or more, 14 parts by weight or more, 15 parts by weight or more, 16 parts by weight or more, 17 parts by weight or more, 18 parts by weight or more, 19 parts by weight or more, or 20 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 polymer in an amount 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, or 16 parts by weight or less, per 100 parts by weight of the alkyl (meth)acrylate units. When the polar group-containing units are present, their proportion may be within the range between any of the lower limits described above and any of the upper limits described above. This range is effective in providing an appropriate antistatic function, preventing static contamination and leaving stains on the adherend during the peeling process, and forming a PSA with appropriate removability and adhesion.

[0056] 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 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, or 50,000 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, 50,000 g / mol or less, or 45,000 g / mol or less. The molecular weight of the polymer may be within a range between any of the lower limits described above and any of the upper limits described above. The weight-average molecular weight is measured by GPC (Gel Permeation Chromatography) using polystyrene as a calibration standard, and a specific measurement method is described in the Examples.

[0057] The polymer may be formed by polymerizing the monomers contained in the blended monomer mixture, taking into consideration the desired composition of polymerized units.

[0058] There is no limitation on the polymerization method, but for example, solution polymerization may be applied.

[0059] When solution polymerization is applied, it is appropriate to carry out a two-step reaction to obtain the polymerized units of Chemical Formula 1.

[0060] For example, a method for obtaining an ionic polymer containing a unit of Formula 1 may include the steps of reacting a monomer mixture containing an alkyl(meth)acrylate and a compound of Formula 3 to obtain a polymer, and reacting the polymer with a haloalkane.

[0061] That is, in order to introduce the unit of Chemical Formula 1 into a polymer, it is possible to consider a method of carrying out polymerization by directly adding an ionic monomer having the structure of Chemical Formula 1 to a monomer mixture for the solution polymerization. However, as a result of confirmation, such ionic monomers generally have reduced solubility in the solvent in which the solution polymerization is carried out, which may result in the formation of a non-uniform polymer or the formed polymer having reduced solubility in the solvent, causing problems during storage.

[0062] However, the above problem can be solved by preparing the polymer through the two-step reaction using the compound of the following Formula 3:

[0063] [ka]

[0064] In Formula 3, 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.

[0065] An example of the compound of Formula 3 is dialkylaminoalkyl(meth)acrylate.

[0066] In Chemical Formula 3, 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.

[0067] In Chemical Formula 3, 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.

[0068] In chemical formula 3, 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.

[0069] In chemical formula 3, 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.

[0070] 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 3 is a precursor for forming the unit of Chemical Formula 1.

[0071] 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 3 may be the same as that for the alkyl(meth)acrylate unit and the unit of Formula 1.

[0072] The monomer mixture may also contain a monomer capable of forming the unit of Formula 2 (e.g., NVP (N-vinyl-2-pyrrolidone), etc.) and / or a monomer capable of forming the polar group-containing unit (e.g., hydroxyalkyl(meth)acrylate, etc.).

[0073] 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 solvent is not limited thereto.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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, or at a concentration of 600 ppm or less, 550 ppm or less, 500 ppm or less, or 450 ppm or less.

[0078] The monomer mixture may further include optional additives such as chain transfer agents.

[0079] The method for polymerizing the monomer mixture is not particularly limited, and the polymerization may be carried out by a known solution polymerization method.

[0080] After forming the polymer in the above manner, the polymer may be reacted with a haloalkane to form the unit of Formula 1.

[0081] The reaction may be carried out by adding the haloalkane to a polymerization solution obtained after producing the polymer, or by recovering the polymer from the polymerization solution and then mixing it again with the haloalkane.

[0082] 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.

[0083] 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.

[0084] The reaction may be carried out by diluting the haloalkane with a suitable solvent and mixing it with a polymerization solution containing the polymer or another solution containing the polymer.

[0085] 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.

[0086] 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.

[0087] By the above method, a polymer having a uniform desired monomer composition and excellent solubility in a solvent can be obtained.

[0088] The present application further relates to an adhesive composition or adhesive.

[0089] The pressure-sensitive adhesive composition or pressure-sensitive adhesive may contain the polymer.

[0090] As used herein, the term "adhesive composition" refers to a composition containing the polymer in a non-crosslinked state, and the term "adhesive" refers to a composition containing the polymer in a crosslinked state.

[0091] The polymer may be present in the pressure-sensitive adhesive composition or pressure-sensitive adhesive at a ratio of 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, 90% by weight or more, or 95% by weight or more. The ratio of the polymer in the pressure-sensitive adhesive composition or pressure-sensitive adhesive may be less than 100% by weight, 99% by weight or less, 98% by weight or less, or 97% by weight or less. The polymer may have a weight ratio within the range between any of the above upper limits and any of the above lower limits.

[0092] When the pressure-sensitive adhesive composition or pressure-sensitive adhesive includes the polymer, it may also include various other necessary additives.

[0093] For example, the pressure-sensitive adhesive composition or pressure-sensitive adhesive may further include a crosslinking agent, if necessary. When a crosslinking agent is included, the polymer in the pressure-sensitive adhesive may be present in a crosslinked state. That is, the crosslinking agent may form a crosslinked structure with the adhesive resin containing the polar group-containing unit.

[0094] The crosslinking agent may be appropriately selected depending on the type of polar group contained in the 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 type of crosslinking agent used in the present application is not limited to the above, and other crosslinking agents may also be used appropriately.

[0095] The isocyanate crosslinking agent may be an aliphatic cyclic polyisocyanate compound and / or an acyclic aliphatic polyisocyanate compound. The term "polyisocyanate" used herein 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.

[0096] 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 per 100 parts by weight of the polymer (based on the solid content of the pressure-sensitive adhesive composition). 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.

[0097] Within this range, the crosslinking agent can efficiently form a desired crosslinked structure together with the polymer.

[0098] In consideration of efficient formation of a desired crosslinked structure and stability before crosslinking, the polymer may further contain a crosslinking retarder.

[0099] 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.

[0100] 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, relative to 100 parts by weight of the polymer (based on the solid content in the pressure-sensitive adhesive composition). 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.

[0101] To achieve an appropriate crosslinking structure with the polymer, 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 of the above upper limits and any of the above lower limits.

[0102] The pressure-sensitive adhesive composition or pressure-sensitive adhesive may contain appropriate additive components in addition to the above components, such as a silane coupling agent, a tackifier, a multifunctional acrylate, an antifoaming agent, an antioxidant, a surfactant, and / or a plasticizer.

[0103] The method for forming the pressure-sensitive adhesive is not particularly limited. For example, the pressure-sensitive adhesive may be formed by applying an appropriate crosslinking method taking into account the type of polymer and / or crosslinking agent used in a pressure-sensitive adhesive composition containing the components that form the pressure-sensitive adhesive. For example, if the polymer and / or crosslinking agent are of a type that crosslinks upon application of heat, a crosslinked product may be formed by applying appropriate heat, or other crosslinking methods may also be used.

[0104] The thickness of the pressure-sensitive adhesive layer is not particularly limited and may be any 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 pressure-sensitive adhesive 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.

[0105] The surface resistance of the adhesive layer of the present application is 5.0 × 10 12 The lower the surface resistance, the better the antistatic performance, so the lower limit is not particularly limited. The surface resistance (Ω / □) of the pressure-sensitive adhesive layer according to one example of the present application is 5.00×10 12 Ω / □ or less, 4.00×10 12 Ω / □ or less, 3.00×10 12 Ω / □ or less, 2.00×10 12 Ω / □ or less or 1.00×10 12 The surface resistance may be Ω / □ or less. The surface resistance may be adjusted depending on the application of the pressure-sensitive adhesive.

[0106] The present application further relates to uses of the polymer or adhesive. The adhesive or polymer may be used in various fields where antistatic properties are required, for example.

[0107] For example, the present application relates to laminates to which said polymers or adhesives have been applied.

[0108] Such a laminate may include, for example, an electronic substrate and an adhesive attached to one or both sides of the electronic substrate.

[0109] In the above, the type of electronic substrate is not particularly limited, and various types that require anti-static properties may be applied.

[0110] 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. [Effects of the Invention]

[0111] The present application may provide a polymer, an adhesive containing the polymer, a method for manufacturing the polymer, and uses of the polymer or adhesive.The present application may provide a polymer capable of forming a material with excellent antistatic function, a method for manufacturing the same, and uses of the polymer.The present application may provide a polymer that exhibits antistatic function without the addition of a separate antistatic agent, does not bleed out of components that exhibit the antistatic function, is easy to store, and can stably maintain the performance of the adhesive after being applied to the adhesive, as well as a method for manufacturing the same and uses of the polymer. [Brief explanation of the drawings]

[0112] [Figure 1] FIG. 1 shows the results of NMR analysis of the polymer produced in the production example. [Figure 2] FIG. 2 shows the results of NMR analysis of the polymer produced in the production example. [Figure 3] FIG. 3 shows the results of NMR analysis of the polymer produced in the production example. DETAILED DESCRIPTION OF THE INVENTION

[0113] 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.

[0114] 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.

[0115] 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.

[0116] 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.

[0117] The evaluation criteria for the stain resistance are as follows.

[0118] <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.

[0119] 4.Reworkability evaluation The reworkability was evaluated by adhering the adhesive layer to an adherend, peeling it off, and observing the surface condition of the peeled adhesive layer. In this evaluation, a glass substrate was used as the adherend, and peeling was performed at a peel angle of approximately 180 degrees and a peel speed of approximately 300 mm / min.

[0120] The evaluation criteria for reworkability are as follows:

[0121] <Reworkability evaluation criteria> ◯: No adhesive residue was observed on the surface of the adherend. △: There is some residue of the adhesive on the surface of the adherend, and it is slightly blurred. X: There is a large amount of residue of the adhesive on the surface of the adherend, and it is blurred.

[0122] 5.GPC (Gel Permeation Chromatograph) The molecular weight was measured using GPC (Gel permeation chromatography). The polymer was placed in 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. The weight-average molecular weight (Mw) and number-average molecular weight (Mn) were determined by comparing the elution time of the sample with the calibration curve.

[0123] <GPC measurement conditions> Equipment: 1200 series of Agilent technologies Columns: Two PLgel mixed B columns from 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)

[0124] Production Example 1. Production of Polymer (A) 2-Ethylhexyl acrylate (EHA), N-vinyl-2-pyrrolidone (NVP), methyl methacrylate (MMA), 2-hydroxyethyl acrylate (HEA), and 2-(dimethylamino)ethyl acrylate (DMAEA) were added in a weight ratio of 72:5:10:10:3 (EHA:NVP:MMA:HEA:DMAEA) to a 1-L reactor equipped with a cooling device for easy temperature control and nitrogen gas reflux. Ethyl acetate (EAc) was added as a solvent. The solvent was added in an amount of approximately 50-60 parts by weight per 100 parts by weight of the total monomers. After purging with nitrogen gas to remove oxygen, the reaction was initiated by adding a reaction initiator (AIBN, azobisisobutyronitrile) at 65°C. The reaction initiator was added in an amount of approximately 400 ppm. The reaction was carried out until the monomer conversion rate reached about 90% or more to obtain a primary polymer.

[0125] The conversion rate was calculated using the following formula 1.

[0126] [Number 1] Conversion rate (%) = 100 × (C / B) / A (Equation 1)

[0127] In Equation 1, A is the solid content of the monomer mixture before polymerization, B is the weight (unit: g) of the primary polymer before drying, and C is the weight (unit: g) of the primary polymer after drying.

[0128] In Equation 1, the solid content (A) is the ratio (=W2 / W1) of the weight of the monomer (W2) to the total weight (W1) of the monomer mixture (including the monomer and the solvent), and the weight (B) of the primary polymer before drying is the weight of the polymer measured after polymerizing the mixture containing the solvent and the monomer.

[0129] Drying for determining the weight (C) in Equation 1 was carried out by holding the polymer at a temperature of about 150° C. for about 30 minutes.

[0130] Bromoethane was added to the primary polymer in an amount of 1 equivalent per 2-(dimethylamino)ethyl acrylate (DMAEA) unit contained in the polymer. After adding bromoethane, the reaction was continued at 80°C for an additional 20 hours to obtain the desired polymer (A).

[0131] The weight average molecular weight (Mw) of the obtained polymer (A) was about 200,000.

[0132] FIG. 1 shows the results of NMR analysis of the polymer (A).

[0133] As can be seen from FIG. 1, the 2-(dimethylamino)ethyl acrylate (DMAEA) unit was converted to the following unit A by the reaction with bromoethane.

[0134] [ka]

[0135] In formula A, R is hydrogen, L is an ethylene group, R1 and R3 are methyl groups, and R2 is an ethyl group.

[0136] Table 1 shows the weight ratios of the polymerized units contained in the polymer during the above-mentioned manufacturing process, where EHA, MMA, NVP, HEA, DMAEA, and Chemical A represent the ratios of 2-ethylhexyl acrylate, N-vinyl-2-pyrrolidone, methyl methacrylate, 2-hydroxyethyl acrylate, 2-(dimethylamino)ethyl acrylate, and Chemical A units, respectively.

[0137] [Table 1]

[0138] Production Example 2: Production of Polymer (B) A primary polymer was prepared in the same manner as in Preparation Example 1, except that the monomer ratio was changed to a weight ratio of 70:5:10:10:5 (EHA:NVP:MMA:HEA:DMAEA) during the preparation of the primary polymer. One equivalent of bromoethane relative to the 2-(dimethylamino)ethyl acrylate (DMAEA) contained in the primary polymer was added to the resulting primary polymer, and the reaction was continued at 80°C for an additional 20 hours to obtain the desired polymer (B).

[0139] The weight average molecular weight (Mw) of the obtained polymer (B) was about 200,000.

[0140] FIG. 2 shows the NMR analysis results for the polymer (B), where the left side shows the results for the first polymer and the right side shows the results for the final polymer (B).

[0141] From the peak shifts in the left and right graphs of FIG. 2, it was confirmed that the 2-(dimethylamino)ethyl acrylate (DMAEA) unit was converted to the unit of formula A by the reaction with bromoethane.

[0142] Table 2 shows the weight ratios of the polymerized units contained in the polymer during the manufacturing process, where EHA, MMA, NVP, HEA, DMAEA, and Chemical A represent the ratios of 2-ethylhexyl acrylate, N-vinyl-2-pyrrolidone, methyl methacrylate, 2-hydroxyethyl acrylate, 2-(dimethylamino)ethyl acrylate, and Chemical A units, respectively.

[0143] [Table 2]

[0144] Production Example 3: Production of Polymer (C) A primary polymer was prepared in the same manner as in Preparation Example 1, except that the monomer ratio was changed to a weight ratio of 65:5:10:10:10 (EHA:NVP:MMA:HEA:DMAEA) during the preparation of the primary polymer. One equivalent of bromoethane relative to the 2-(dimethylamino)ethyl acrylate (DMAEA) contained in the primary polymer was added to the resulting primary polymer, and the reaction was continued at 80°C for an additional 20 hours to obtain the desired polymer (C).

[0145] The weight average molecular weight (Mw) of the obtained polymer (C) was about 200,000.

[0146] FIG. 3 shows the results of NMR analysis of the polymer (C).

[0147] As can be seen from FIG. 3, the 2-(dimethylamino)ethyl acrylate (DMAEA) unit was converted to the compound A unit by the reaction with bromoethane.

[0148] Table 3 below shows the weight ratios of the polymerized units contained in the polymer during the manufacturing process, where EHA, MMA, NVP, HEA, DMAEA, and Chemical A represent the ratios of 2-ethylhexyl acrylate, N-vinyl-2-pyrrolidone, methyl methacrylate, 2-hydroxyethyl acrylate, 2-(dimethylamino)ethyl acrylate, and Chemical A units, respectively.

[0149] [Table 3]

[0150] Production Example 4: Production of polymer (D) 2-Ethylhexyl acrylate (EHA), N-vinyl-2-pyrrolidone (NVP), methyl methacrylate (MMA), and 2-hydroxyethyl acrylate (HEA) were added in a weight ratio of 75:5:10:10 (EHA:NVP:MMA:HEA) to a 1 L reactor equipped with a cooling device for easy temperature control and refluxing nitrogen gas. Ethyl acetate (EAc) was then added as a solvent. After purging with nitrogen gas to remove oxygen, the reaction was initiated by adding azobisisobutyronitrile (AIBN) as a reaction initiator at 65°C.

[0151] The reaction was continued until the conversion rate reached 90% or more to obtain the desired polymer (D). The conversion rate was measured in the same manner as in Production Example 1. The weight average molecular weight (Mw) of polymer (D) was about 200,000.

[0152] Production Example 5: Production of Polymer (E) Polymer (E) was produced in the same manner as in Production Example 4, except that 2-ethylhexyl acrylate (EHA), N-vinyl-2-pyrrolidone (NVP), and 2-hydroxyethyl acrylate (HEA) were added to the reactor in a weight ratio of 85:5:10 (EHA:NVP:HEA). The weight average molecular weight (Mw) of polymer (E) was about 200,000.

[0153] Production Example 6: Production of polymer (F) Polymer (F) was produced in the same manner as in Production Example 4, except that 2-ethylhexyl acrylate (EHA), methyl methacrylate (MMA), and 2-hydroxyethyl acrylate (HEA) were added to the reactor in a weight ratio of 80:10:10 (EHA:MMA:HEA). The weight average molecular weight (Mw) of polymer (F) was about 200,000.

[0154] Example 1 Polymer (A) of Preparation Example 1 was diluted to an appropriate concentration with approximately 0.25 parts by weight of a crosslinker (DR-7030HD, San-ei Ink) and approximately 3 parts by weight of acetylacetone per 100 parts by weight of the solid content of polymer (A), and the mixture was uniformly mixed to prepare a pressure-sensitive adhesive composition. The pressure-sensitive adhesive composition was then coated onto release paper and heated to 120°C for approximately 4 minutes and 30 seconds to prepare a pressure-sensitive adhesive layer with a thickness of approximately 100 μm.

[0155] Example 2 A pressure-sensitive adhesive layer was produced in the same manner as in Example 1, except that the polymer (B) of Preparation Example 2 was used instead of the polymer (A) of Preparation Example 1.

[0156] Example 3 A pressure-sensitive adhesive layer was produced in the same manner as in Example 1, except that the polymer (C) of Preparation Example 3 was used instead of the polymer (A) of Preparation Example 1.

[0157] Comparative Example 1 Polymer (D) of Preparation Example 4 was mixed with about 0.25 parts by weight of a crosslinker (DR-7030HD, San-ei Ink), about 3 parts by weight of acetylacetone, and about 0.05 parts by weight of a lithium salt (Lithium bis(trifluoromethanesulfonyl)imide) per 100 parts by weight of the solids content of the polymer (D), diluted to an appropriate concentration, and uniformly mixed to prepare a pressure-sensitive adhesive composition. Next, the pressure-sensitive adhesive composition was coated onto release paper and held at 120°C for about 4 minutes and 30 seconds to produce a pressure-sensitive adhesive layer with a thickness of about 100 μm.

[0158] A pressure-sensitive adhesive layer was formed in the same manner as in Example 1 using the pressure-sensitive adhesive composition.

[0159] Comparative Example 2 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 amount of lithium salt was changed to about 0.15 parts by weight per 100 parts by weight of the polymer.

[0160] Comparative Example 3 Polymer (E) of Preparation Example 5 was mixed with about 0.25 parts by weight of a crosslinker (DR-7030HD, San-ei Ink), about 3 parts by weight of acetylacetone, and about 0.15 parts by weight of a lithium salt (Lithium Bis(trifluoromethanesulfonyl)imide) per 100 parts by weight of the solid content of the polymer (E), diluted to an appropriate concentration, and uniformly mixed to prepare a pressure-sensitive adhesive composition. The pressure-sensitive adhesive composition was then coated onto release paper and heated to 120°C for about 4 minutes and 30 seconds to prepare a pressure-sensitive adhesive layer with a thickness of about 100 μm.

[0161] A pressure-sensitive adhesive layer was formed in the same manner as in Example 1 using the pressure-sensitive adhesive composition.

[0162] Comparative Example 4 A pressure-sensitive adhesive layer was prepared in the same manner as in Comparative Example 3, except that the polymer (F) of Preparation Example 6 was used instead of the polymer (E) of Preparation Example 5.

[0163] The evaluation results for the Examples and Comparative Examples are summarized in Table 4 below.

[0164] [Table 4]

Claims

1. A polymer comprising alkyl (meth)acrylate units and units of the following formula 1: 【Chemistry 1】 In Chemical 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 of claim 1, comprising 60 to 90% by weight of alkyl (meth)acrylate units.

3. The polymer according to claim 1, wherein the alkyl(meth)acrylate units comprise alkyl(meth)acrylate units having an alkyl group with 1 to 3 carbon atoms and alkyl(meth)acrylate units having an alkyl group with 4 or more carbon atoms.

4. 4. The polymer according to claim 3, wherein the ratio (A2 / A1) of the weight (A1) of the alkyl (meth)acrylate units having an alkyl group with 1 to 3 carbon atoms to the weight (A2) of the alkyl (meth)acrylate units having an alkyl group with 4 or more carbon atoms is within the range of 2 to 20.

5. In Chemical Formula 1, L is an alkylene group having 2 to 8 carbon atoms or an alkylidene group having 1 to 8 carbon atoms, R is a hydrogen atom or a methyl group, and R １ ~R ３ and each independently represent an alkyl group having 1 to 4 carbon atoms.

6. 2. The polymer of claim 1, comprising 1 to 30 parts by weight of units of Formula 1 per 100 parts by weight of alkyl (meth)acrylate units.

7. The polymer of claim 1 further comprising a unit of Formula 2: 【Chemistry 2】 In Chemical Formula 2, 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.

8. In Chemical Formula 2, 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 polymer of claim 7 , wherein at least one of is a carbonyl group.

9. 8. The polymer of claim 7, comprising 0.5 to 20 parts by weight of units of Formula 2 per 100 parts by weight of alkyl (meth)acrylate units.

10. The polymer of claim 1 further comprising a polar group-containing unit.

11. The polymer of claim 10, comprising 1 to 30 parts by weight of polar group-containing units per 100 parts by weight of alkyl (meth)acrylate units.

12. Reacting a monomer mixture containing alkyl(meth)acrylate and a compound represented by Formula 3 to obtain a polymer; reacting said polymer with a haloalkane. 【Transformation 3】 In Chemical Formula 3, 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.

13. The method for producing a polymer according to claim 12, wherein the reaction of the monomer mixture is a solution polymerization reaction.

14. A pressure-sensitive adhesive comprising the polymer of claim 1.

15. The pressure-sensitive adhesive according to claim 14, wherein the polymer is contained in a crosslinked state.

16. The pressure sensitive adhesive of claim 14, further comprising a crosslinking agent and a crosslinking retarder that crosslinks the polymer.

17. The pressure-sensitive adhesive according to claim 16, wherein the crosslinking agent is contained in a proportion of 0.01 to 10 parts by weight per 100 parts by weight of the polymer, the crosslinking retarder is contained in a proportion of 0.1 to 10 parts by weight per 100 parts by weight of the polymer, 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.

18. The pressure-sensitive adhesive according to claim 14, wherein the polymer has a weight average molecular weight in the range of 10,000 g / mol to 200,000 g / mol.

19. An electronic board; A laminate comprising the pressure-sensitive adhesive according to claim 14 attached to one or both surfaces of the electronic substrate.

20. an OLED panel; 15. An OLED device comprising the adhesive of claim 14 attached to one or both sides of the OLED panel.

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