Polymer

Abstract

The present application may provide a polymer, a pressure sensitive adhesive comprising the same, a method for producing the polymer, and a use of the polymer or the pressure sensitive adhesive. The present application can provide a polymer capable of forming a material having an excellent antistatic function, a method for producing the same, and a use of the polymer. The present application can provide: a polymer which can exhibit an antistatic function without the addition of a separate antistatic agent, does not bleed out a component exhibiting an antistatic function, is easy to store, and can be used in the field of electronic devices, a method for producing the same, and a use of the polymer. And the performance and the like of the pressure-sensitive adhesive can be maintained after the composition is applied to the related pressure-sensitive adhesive.

Description

Technical Field

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0129930, filed on October 11, 2022, the disclosure of which is incorporated herein by reference in its entirety. Technical Field

[0004] The present application relates to a polymer, a pressure-sensitive adhesive comprising the same, a method for producing the polymer, and the use of the polymer or the pressure-sensitive adhesive. Background Art

[0005] Materials with antistatic function can be applied in many fields. For example, materials with antistatic function and pressure-sensitive adhesive or adhesive properties are also used in optical devices such as LCD (liquid crystal display) and OLED (organic light emitting diode).

[0006] LCD includes a liquid crystal panel having a liquid crystal layer and a polarizing plate, wherein when attaching the liquid crystal panel and the polarizing plate, a pressure-sensitive adhesive having an antistatic function may be used, etc. In devices such as OLED, a pressure-sensitive adhesive having an antistatic function may also be applied to an OLED panel, etc.

[0007] The general method for producing materials such as pressure-sensitive adhesives or adhesives with antistatic function is to mix antistatic agents with polymers such as acrylic polymers with pressure-sensitive adhesive properties, wherein various ionic compounds or surfactants etc. are known as available antistatic agents. However, these antistatic agents may cause pollution etc., or may cause problems such as protuberance, bubbles, or peeling by seeping out from pressure-sensitive adhesives or adhesives etc. during use or storage. In addition, antistatic agents may affect the performance of pressure-sensitive adhesives or adhesives, particularly deteriorate the reprocessability (reprocessing) etc. of pressure-sensitive adhesives.

[0008] In order to solve such a problem, it is also known that a monomer having an antistatic function (for example, an ionic monomer) is directly polymerized into an acrylic polymer to form a pressure-sensitive adhesive, etc. In such a method, an ionic monomer, etc. is directly introduced therein during the polymerization process and polymerized. However, in such a method, since the ionic monomer, etc. generally has a poor affinity for the solvent serving as a polymerization medium, there is a problem in that a heterogeneous polymer is formed, or the formed polymer shows insolubility in the solvent, making storage difficult.

[0009] Therefore, there is a need for a material that can solve such problems. Summary of the invention

[0010] Technical issues

[0011] The present application relates to a polymer, a pressure-sensitive adhesive comprising the same, a method for producing the polymer, and the use of the polymer or the pressure-sensitive adhesive.

[0012] The present application aims to provide a polymer capable of forming a material having an excellent antistatic function, a method for producing the same, and the use of the polymer. The present application aims to provide a polymer, a method for producing the same, and the use of the polymer, which can exhibit an antistatic function without adding a separate antistatic agent, does not ooze out a component that exerts an antistatic function, is easy to store, and can be applied to a pressure-sensitive adhesive, etc., and then stably maintains the performance of the relevant pressure-sensitive adhesive.

[0013] Technical Solution

[0014] Among the physical properties mentioned in this specification, unless otherwise specified, the physical properties in which temperature affects the physical properties are physical properties measured at room temperature.

[0015] In this specification, the term room temperature is a natural temperature without heating or cooling, which means, for example, any temperature in the range of about 10° C. to 30° C., such as a temperature around about 15° C., about 18° C., about 20° C., about 23° C., or about 25° C. In addition, unless otherwise specified in this specification, the unit of temperature is ° C.

[0016] In the physical properties mentioned in this specification, in the case where pressure affects the results, unless otherwise specified, the relevant physical properties are physical properties measured under normal pressure. The term normal pressure is the natural pressure without pressurization or decompression, wherein usually about 1 atmosphere (about 700 mmHg to 800 mmHg) is called normal pressure.

[0017] Among the physical properties mentioned in this specification, in the case where humidity affects the results, unless otherwise specified, the relevant physical properties are physical properties measured at room temperature and normal pressure without special adjustment of humidity.

[0018] The application relates to polymer.As known, the term polymer can mean the material that two or more units (monomer or oligomer etc.) are connected and formed by covalent bonds.In an example, polymer can mean the material that comprises the structure that wherein two or more units are connected by covalent bonds and has a certain level or higher molecular weight.

[0019] The polymer may be an acrylic polymer. The term acrylic polymer means a polymer comprising a polymerization unit of an acrylic monomer as a main component.

[0020] Here, the polymerization unit means a unit formed by including a monomer in a polymer in a state in which the monomer forms a covalent bond by polymerization.

[0021] In the present specification, the acrylic monomer means (meth)acrylic acid or a derivative thereof (for example, alkyl acrylate or alkyl methacrylate, etc.).

[0022] In the present specification, the term (meth)acrylic acid may mean acrylic acid or methacrylic acid, or may mean both.

[0023] Here, the case where the polymer contains polymerization units of an acrylic monomer as a main component means the case where the ratio of the polymerization units of the acrylic monomer is 100% by weight or less, and at the same time is 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, 95% by weight or more, based on the total weight of all polymerization units present in the polymer.

[0024] In one example, the polymer may include an alkyl (meth)acrylate unit. The unit is a polymerized unit formed by polymerizing an alkyl (meth)acrylate.

[0025] In the present application, as the alkyl(meth)acrylate, for example, an alkyl(meth)acrylate in which the carbon number of the alkyl moiety is in the range of 1 to 20, 1 to 16, 1 to 12, 4 to 12, or 4 to 8 can be used. The alkyl group of the alkyl(meth)acrylate may be linear, branched, or cyclic.

[0026] Specific examples of alkyl (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, tert-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, isooctyl (meth)acrylate, etc., but are not limited thereto.

[0027] In one example, the polymer may contain an alkyl (meth)acrylate unit having an alkyl group having 1 to 3 carbon atoms (first unit) and an alkyl (meth)acrylate unit having an alkyl group having 4 or more carbon atoms (second unit) as the alkyl (meth)acrylate unit. Thus, a polymer having properties suitable for application as a pressure-sensitive adhesive while effectively ensuring desired functions (antistatic function, etc.) while adjusting properties such as glass transition temperature to an appropriate level can be obtained.

[0028] In one example, the alkyl(meth)acrylate unit having an alkyl group having 1 to 3 carbon atoms as the first unit may be an alkyl methacrylate unit having an alkyl group having 1 to 3 carbon atoms.

[0029] The carbon number of the alkyl group included in the (meth)acrylic acid alkyl ester unit as the second unit may be 4 to 20, 4 to 16, 4 to 12, 4 to 8, or 6 to 8. In addition, the second unit may be an acrylic acid alkyl ester unit.

[0030] The weight ratio of the alkyl (meth)acrylate units relative to the weight of all polymerized units contained in the polymer may be adjusted. The weight ratio may be 60 wt % or more, 61 wt % or more, 63 wt % or more, 64 wt % or more, 65 wt % or more, 66 wt % or more, 67 wt % or more, 68 wt % or more, 69 wt % or more, 70 wt % or more, 71 wt % or more, 72 wt % or more, 73 wt % or more, 74 wt % or more, 75 wt % or more, 76 wt % or more, 77 wt % or more, 78 wt % or more, or 79 wt % or more, and may The weight ratio may be about 90 wt % or less, 89 wt % or less, 88 wt % or less, 87 wt % or less, 86 wt % or less, 85 wt % or less, 84 wt % or less, 83 wt % or less, 82 wt % or less, 81 wt % or less, 80 wt % or less, 79 wt % or less, 78 wt % or less, 77 wt % or less, 76 wt % or less, 75 wt % or less, 74 wt % or less, 73 wt % or less, 72 wt % or less, or about 71 wt % or less. The weight ratio may be within the range of any one of the above-mentioned lower limit and any one of the above-mentioned upper limit.

[0031] The ratio (A2 / A1) of the second unit weight (A2) to the first unit weight (A1) in the polymer can be adjusted. The ratio (A2 / A1) can be 2 or more, 3 or more, 4 or more, 5 or more, or 6 or more. The ratio (A2 / A1) can 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 can be within the range of any one of the above-mentioned lower limits and any one of the above-mentioned upper limits. Thus, it is possible to obtain a polymer having a characteristic of effectively ensuring desired functions (antistatic function, etc.) and being suitable for application as a pressure-sensitive adhesive while adjusting characteristics such as glass transition temperature to an appropriate level.

[0032] The polymer may further include units of the following Formula 1 in addition to the alkyl (meth)acrylate units.

[0033] [Formula 1]

[0034]

[0035] In 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.

[0036] In this specification, the term alkylene means a divalent group formed by removing a hydrogen atom from each of two different carbon atoms of an alkane. The carbon number of the alkylene group can be 2 to 20, 2 to 16, 2 to 12, 2 to 8, or 2 to 4. The alkylene group can be linear, branched or cyclic. The alkylene group can be optionally substituted with one or more substituents.

[0037] In this specification, the term alkylidene means a divalent group formed by removing two hydrogen atoms from one carbon atom of an alkane. The carbon number of the alkylidene can be 1 to 20, 1 to 16, 1 to 12, 1 to 8 or 1 to 4. The alkylidene can be linear, branched or cyclic. The alkylidene can optionally be substituted with one or more substituents.

[0038] The alkylidene group or alkylene group of Formula 1 may be the above-mentioned alkylidene group or alkylene group.

[0039] In 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 one or more substituents.

[0040] In Formula 1, R1 to R3 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 one or more substituents.

[0041] In one example, one of R1 to R3 in Formula 1 may be an ethyl group, and the other two may be methyl groups.

[0042] By introducing such a structure, the polymer can exhibit physical properties suitable for forming a pressure-sensitive adhesive while ensuring the desired antistatic function.

[0043] Relative to 100 parts by weight of the (meth)acrylic acid alkyl ester unit, the polymer of the present application may include the unit of Formula 1 in the following amount: 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. Relative to 100 parts by weight of (meth) alkyl ester units, the polymer of the present application may include units of Formula 1 in the following amounts: 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. The ratio of the units of Formula 1 may also be within the range of any one of the above lower limits and any one of the above upper limits. Within this range, a polymer that exhibits an appropriate antistatic function and is suitable for forming a pressure-sensitive adhesive can be provided. A pressure-sensitive adhesive formed from such a polymer can exhibit appropriate adhesive and antistatic functions, does not cause contamination caused by static electricity or contamination of an adherend during peeling, and can also stably ensure reworkability.

[0044] In addition to the above polymerized units, the polymer may further contain other desired polymerized units.

[0045] For example, the polymer may comprise units of Formula 2 below.

[0046] [Formula 2]

[0047]

[0048] In 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 does not exist, and the bond between R4 and R5 and the bond between R8 and R9 are each independently a single bond or a double bond.

[0049] In Formula 2, the absence of R6 means that R5 and R9 are directly connected.

[0050] In Formula 2, when R4, R5, R6, R8, and R9 are carbon atoms, hydrogen atoms may be bonded to the relevant carbon atoms to match valence, considering the overall structure of the compound of Formula 2.

[0051] In one example, in Formula 2, R4, R5, R8 and R9 may each independently be a carbon atom or a carbonyl group, R6 may be a single bond or a carbon atom, 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, but at least one of R4, R5, R8 and R9 may be a carbonyl group.

[0052] In one example, in Formula 2, either one of R4 and R8 may be a carbon atom, the other may be a carbonyl group, R6 may be a single bond, and the bond between R4 and R5 and the bond between R8 and R9 may be a single bond.

[0053] In one example, in Formula 2, R4, R5, R8, and R9 may each be a carbon atom, R6 may be a single bond, and a bond between R4 and R5 and a bond between R8 and R9 may each be a double bond.

[0054] In one example, in Formula 2, R4, R5, R8, and R9 may each be a carbon atom, R6 may be a single bond, and a bond between R4 and R5 and a bond between R8 and R9 may each be a single bond.

[0055] In one example, in Formula 2, R4, R5, R6, R8, and R9 may each be a carbon atom, and a bond between R4 and R5 and a bond between R8 and R9 may each be a single bond.

[0056] In one example, in Formula 2, R4, R5, R8, and R9 may each be a carbon atom, R6 may be an oxygen atom, and a bond between R4 and R5 and a bond between R8 and R9 may each be a single bond.

[0057] When the unit of the above formula 2 exists, relative to 100 parts by weight of (meth) alkyl acrylate units, the ratio of the unit can 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. When the unit of the above formula 2 exists, relative to 100 parts by weight of (meth) alkyl acrylate units, the ratio of the unit can 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. When the unit of formula 2 exists, the ratio can be within the range of any one of the above lower limits and any one of the above upper limits. This range is advantageous for forming a pressure-sensitive adhesive that exhibits an appropriate antistatic function, does not cause contamination due to static electricity or contamination due to peeling, and exhibits appropriate adhesiveness and reworkability.

[0058] If necessary, the polymer of the present application may also include units containing polar groups. Such units may be necessary to control the cohesive force of the pressure-sensitive adhesive or to realize a cross-linked structure. Units containing polar groups refer to polymerized units formed by monomers having polar groups. Units containing polar groups may be hydroxyl-containing units or carboxyl-containing units, etc. It is particularly advantageous to use units containing hydroxyl groups, but it is not limited thereto. Since carboxyl-containing units may also cause corrosion in electronic devices or optical devices, etc., they may not be present in the polymer depending on the use of the polymer.

[0059] The hydroxyl-containing monomer capable of forming a hydroxyl-containing unit may 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, or 2-hydroxypolypropylene glycol (meth)acrylate, and the like, and hydroxyalkyl (meth)acrylate may be used generally. In hydroxyalkyl (meth)acrylate, the carbon number of the alkyl group may be 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.

[0060] Examples of the carboxyl-containing monomer capable of forming the carboxyl-containing unit may include (meth)acrylic acid, 2-(meth)acryloyloxyacetic acid, 3-(meth)acryloyloxypropionic acid, 4-(meth)acryloyloxybutyric acid, acrylic acid dimer, itaconic acid, maleic acid and / or maleic anhydride, and the like.

[0061] The polar group-containing units may be contained in the polymer in an amount 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. Relative to 100 weight parts of (meth) alkyl acrylate units, the unit containing polar groups can be included in polymer by following amount: 30 weight parts or less, 29 weight parts or less, 28 weight parts or less, 27 weight parts or less, 26 weight parts or less, 25 weight parts or less, 24 weight parts or less, 23 weight parts or less, 22 weight parts or less, 21 weight parts or less, 20 weight parts or less, 19 weight parts or less, 18 weight parts or less, 17 weight parts or less or 16 weight parts or less.When the unit containing polar groups exists, the ratio can be in the scope of any one in the above-mentioned lower limit and any one in the above-mentioned upper limit.This scope can effectively form such pressure-sensitive adhesive: it does not leave the pollution caused by static electricity or the pollution to adherend during the stripping process while showing suitable antistatic function, and has suitable reprocessability and adhesion.

[0062] The molecular weight of the polymer can be adjusted within an appropriate range. For example, the molecular weight of the polymer is a weight average molecular weight (Mw), which can 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 can be about 200,000g / mol or less, 150,000g / mol or less, 100,000g / mol or less, 90,000g / mol or less, 80,000g / mol or less, 70,000g / mol or less, 60,000g / mol or less, 50,000g / mol or less, or 45,000g / mol or less. The molecular weight of the polymer can be within the range of any one of the above lower limits and any one of the above upper limits. The weight average molecular weight is a value measured by GPC (Gel Permeation Chromatograph) using polystyrene as a calibration standard sample, and specific measuring methods are described in the embodiments.

[0063] Such a polymer can be formed by polymerizing monomers contained in a monomer mixture formulated in consideration of a desired composition of polymerization units.

[0064] The polymerization method is not limited, but, for example, solution polymerization can be applied.

[0065] When solution polymerization is employed, it may be appropriate to conduct a two-step reaction to obtain the polymerized units of Formula 1 above.

[0066] For example, a method of obtaining a polymer including a unit of Formula 1 above may include the steps of reacting a monomer mixture including an alkyl (meth)acrylate and a compound of Formula 3 below to obtain a polymer, and reacting the polymer with an alkyl halide.

[0067] That is, in order to introduce the unit of the above formula 1 into the polymer, a method of directly introducing an ionic monomer including the structure of formula 1 into a monomer mixture for solution polymerization and performing polymerization can be considered. However, as a confirmed result, such an ionic monomer generally has poor solubility in a solvent for solution polymerization and thus forms a heterogeneous polymer, or the solubility of the formed polymer in the solvent is reduced, thereby causing storage problems.

[0068] However, the above problems can be solved by producing a polymer through the above two-step reaction using a compound of Formula 3 below.

[0069] [Formula 3]

[0070]

[0071] In Formula 3, L1 can be an alkylene group or an alkylidene group, and R 12 can be a hydrogen atom or an alkyl group, and R 10 and R 11 Each may independently be an alkyl group.

[0072] Examples of the compound of the above Formula 3 include dialkylaminoalkyl (meth)acrylates and the like.

[0073] In 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 one or more substituents.

[0074] In 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. The alkylidene group may be linear, branched, or cyclic. The alkylidene group may be optionally substituted with one or more substituents.

[0075] In 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 optionally be substituted with one or more substituents.

[0076] In formula 3, R 10 and R 11 Can be each independently 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 can be a methyl or ethyl group. The alkyl group can be linear, branched or cyclic. The alkyl group can be optionally substituted with one or more substituents.

[0077] In the method for producing a polymer, the alkyl (meth)acrylate contained in the monomer mixture is a monomer forming the alkyl (meth)acrylate unit, and the compound of Formula 3 is a precursor for forming the unit of Formula 1 above.

[0078] Therefore, the specific type of the alkyl (meth)acrylate in the monomer mixture can be controlled to be able to form the alkyl (meth)acrylate unit, and the content of the alkyl (meth)acrylate unit and the unit of Formula 1 can be applied to the ratio of the alkyl (meth)acrylate and the compound of Formula 3.

[0079] In addition, the monomer mixture may also contain monomers capable of forming units of Formula 2 (eg, NVP (N-vinyl-2-pyrrolidone)) and / or monomers capable of forming units containing polar groups (eg, hydroxyalkyl (meth)acrylate).

[0080] In such a monomer mixture, a solvent may also be present. As the solvent, a solvent suitable for conventional solution polymerization may be used, and for example, one, or two or more selected from the following may be used: a substituted or unsubstituted aliphatic C1 to C 20 Saturated hydrocarbon solvents such as n-hexane, n-heptane, cyclohexane and isooctane; 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, etc., but are not limited thereto.

[0081] During the polymerization, 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 relative to 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 relative to 100 parts by weight of the total monomers. The ratio of the solvent may be adjusted as needed.

[0082] A reaction initiator may also be present in the monomer mixture. The type of the reaction initiator is not particularly limited, and for example, a free radical initiator may be used. As the free radical initiator, a free radical thermal initiator or a free radical photoinitiator may be used, and its specific type is not particularly limited.

[0083] For example, as the initiator, for example, 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) and the like can be used, but is not limited thereto.

[0084] The reaction initiator can be present in an appropriate ratio according to the desired polymer, and can be included in a concentration of, for example, 200 ppm or more, 250 ppm or more, 300 ppm or more, or 350 ppm or more. In another example, the reaction initiator can be included in a concentration of 600 ppm or less, 550 ppm or less, 500 ppm or less, or 450 ppm or less.

[0085] In the monomer mixture, optional additives such as a chain transfer agent may also be included.

[0086] The method for conducting polymerization of such a monomer mixture is not particularly limited, and the polymerization can be conducted according to a known solution polymerization method.

[0087] After forming the polymer by such a method, the relevant polymer can be reacted with an alkyl halide to form the unit of Formula 1 above.

[0088] The reaction can also be carried out by preparing a polymer and then adding an alkyl halide to the obtained polymerization solution, and can also be carried out by recovering a polymer from the polymerization solution and then mixing it with an alkyl halide.

[0089] As the alkyl halide, a compound in which one of the hydrogen atoms of the alkane is replaced by a halogen can be used. In this case, the halogen to be replaced can be exemplified by Br, Cl, F, or I, but is not limited thereto.

[0090] As the alkyl halide, an alkyl halide 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 can be used, and for example methyl halide or ethyl halide can be used. The alkyl halide can be linear, branched or cyclic, and can be optionally substituted with one or more substituents.

[0091] The reaction can be performed by mixing an alkyl halide in a state of being diluted in an appropriate solvent with a polymerization solution containing the polymer or other solutions containing the polymer.

[0092] Such a reaction can be carried out, for example, at a temperature of about 50°C or more, 55°C or more, 60°C or more, 65°C or more, 70°C or more, 75°C or more, or 80°C or more. The reaction temperature can also be about 200°C or less, 190°C or less, 180°C or less, 170°C or less, 160°C or less, 150°C or less, 140°C or less, 130°C or less, 120°C or less, 110°C or less, 100°C or less, 95°C or less, 90°C or less, 85°C or less, or 80°C or less. The range of the reaction temperature can also be within the range of any one of the above upper limits and any one of the above lower limits.

[0093] The reaction can be carried out for example for about 1 hour or longer, 5 hours or longer, 15 hours or longer or 20 hours or longer. The reaction times can also be 200 hours or shorter, 150 hours or shorter, 100 hours or shorter, 90 hours or shorter, 80 hours or shorter, 70 hours or shorter, 60 hours or shorter, 50 hours or shorter, 40 hours or shorter, 30 hours or shorter or about 20 hours or shorter. The scope of the reaction times can also be in the scope of any one of the above-mentioned upper limit and any one of the above-mentioned lower limit.

[0094] By such a method, a polymer which uniformly has a desired monomer composition and has excellent solubility in a solvent can be obtained.

[0095] The present application also relates to a pressure-sensitive adhesive composition or a pressure-sensitive adhesive.

[0096] The pressure-sensitive adhesive composition or the pressure-sensitive adhesive may include the polymer.

[0097] In the present specification, the term pressure-sensitive adhesive composition may mean a composition in which a polymer is included in a non-crosslinked state, and the pressure-sensitive adhesive may mean a composition in which a polymer is included in a crosslinked state.

[0098] In pressure-sensitive adhesive composition or pressure-sensitive adhesive, polymer can exist in the following ratio: about 50 % by weight or larger, 55 % by weight or larger, 60 % by weight or larger, 65 % by weight or larger, 70 % by weight or larger, 75 % by weight or larger, 80 % by weight or larger, 85 % by weight or larger, 90 % by weight or larger or 95 % by weight or larger. The ratio of polymer can be less than 100 % by weight, 99 % by weight or smaller, 98 % by weight or smaller or 97 % by weight or smaller in pressure-sensitive adhesive composition or pressure-sensitive adhesive. Polymer also can have the weight ratio in the scope of any one in the above-mentioned upper limit and any one in the above-mentioned lower limit.

[0099] The pressure-sensitive adhesive composition or the pressure-sensitive adhesive may include various other necessary additives as long as it includes the polymer.

[0100] For example, if necessary, the pressure-sensitive adhesive composition or the pressure-sensitive adhesive may further include a crosslinking agent. When the crosslinking agent is included, the polymer may be present in the pressure-sensitive adhesive in a crosslinked state. That is, the crosslinking agent may realize a crosslinked structure with the pressure-sensitive adhesive resin containing a unit containing a polar group.

[0101] As a cross-linking agent, an appropriate type can be selected according to the type of polar group contained in the polymer. For example, when the polar group is a hydroxyl group, an isocyanate cross-linking agent can be typically used as a cross-linking agent. However, the type of the cross-linking agent used in the present application is not limited to the above, and other cross-linking agents can also be appropriately used.

[0102] As isocyanate crosslinking agents, aliphatic cyclic polyvalent isocyanate compounds and / or aliphatic non-cyclic polyvalent isocyanate compounds can be used. Here, polyvalent means that the compound contains two or more isocyanate groups. The number of isocyanate groups present in the compound can 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. The aliphatic cyclic isocyanate compound can be exemplified by an isocyanate compound such as isophorone diisocyanate, methylene dicyclohexyl diisocyanate, or cyclohexane diisocyanate, or a derivative thereof such as a dimer or trimer, or a reactant of any of the foregoing with a polyol (e.g., trimethylolpropane), and the aliphatic non-cyclic isocyanate compound can be exemplified by an alkylene diisocyanate compound 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, or a derivative thereof such as a dimer or trimer, or a reactant of any of the foregoing with a polyol (e.g., trimethylolpropane), but is not limited thereto.

[0103] Relative to the polymer (based on the solid content in the pressure-sensitive adhesive composition) of 100 weight portions, the use ratio of crosslinking agent can be 0.01 weight portion or more, 0.05 weight portion or more, 0.1 weight portion or more, 0.15 weight portion or more, 0.2 weight portion or more or 0.25 weight portion or more.In another example, ratio can be 10 weight portions or less, 9 weight portions or less, 8 weight portions or less, 7 weight portions or less, 6 weight portions or less, 5 weight portions or less, 4 weight portions or less, 3 weight portions or less, 2 weight portions or less, 1 weight portion or less, 0.9 weight portion or less, 0.8 weight portion or less, 0.7 weight portion or less, 0.6 weight portion or less, 0.5 weight portion or less, 0.4 weight portion or less or 0.3 weight portion or less left and right.The ratio of crosslinking agent can be in the scope of any one in the above-mentioned upper limit and any one in the above-mentioned lower limit.

[0104] Within such a range, the cross-linking agent can effectively form a desired cross-linked structure together with the polymer.

[0105] The polymer may further contain a cross-linking inhibitor in consideration of efficient formation of a desired cross-linking structure, stability before cross-linking, and the like.

[0106] As the crosslinking inhibitor, a known compound can be used, and for example, one or two or more selected from the following can be used: 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.

[0107] Relative to 100 parts by weight of polymer (based on the solid content in the pressure-sensitive adhesive composition), the use ratio of crosslinking inhibitor can be 0.1 parts by weight or more, 0.5 parts by weight or more, 1 parts 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. In another example, ratio can be 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 or so. The ratio of crosslinking inhibitor can be in the scope of any one of the above-mentioned upper limit and any one of the above-mentioned lower limit.

[0108] In order to achieve an appropriate cross-linked structure with the polymer, the ratio (A / B) of the weight of the cross-linking inhibitor (A) to the weight of the cross-linking agent (B) 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 also 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 also be within the range of any one of the above upper limits and any one of the above lower limits.

[0109] In addition to the above components, the pressure-sensitive adhesive composition or pressure-sensitive adhesive may further include appropriate additional components, and for example, may further include a silane coupling agent, a tackifier, a multifunctional acrylate, a defoaming agent, an antioxidant, a surfactant and / or a plasticizer.

[0110] The method of forming the pressure sensitive adhesive is not particularly limited. For example, the pressure sensitive adhesive can be formed by applying a pressure sensitive adhesive composition that formulates the components to form the pressure sensitive adhesive to an appropriate crosslinking method that takes into account the type of polymer and / or crosslinking agent applied. For example, if the polymer and / or crosslinking agent is of a type that crosslinks by applying heat, a crosslinked product can be formed by applying appropriate heat, and other crosslinking methods can also be applied thereto.

[0111] The thickness of the adhesive layer is not particularly limited, and it can have an appropriate thickness. For example, it can be 10 μm or more, 30 μm or more, 50 μm or more, 70 μm or more, or 90 μm or more. In another example, the thickness of the pressure-sensitive adhesive layer can 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.

[0112] The surface resistance of the pressure-sensitive adhesive layer of the present application may be 5.0×10 12 Ω / □ or less. The lower the surface resistance, the better the antistatic performance, so that its lower limit is not particularly limited. The surface resistance (Ω / □) of the pressure-sensitive adhesive layer according to one example of the present application may be 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 Ω / □ or less. The surface resistance can be adjusted according to the application of the pressure-sensitive adhesive.

[0113] The present application also relates to the use of the polymer or the pressure-sensitive adhesive. For example, the pressure-sensitive adhesive or the polymer can be used in various fields requiring antistatic function.

[0114] For example, the present application may involve laminates employing polymers or pressure sensitive adhesives.

[0115] Such a laminate may include, for example, an electronic substrate and a pressure sensitive adhesive attached to one or both sides of the electronic substrate.

[0116] Here, the type of the electronic substrate is not particularly limited, and various types that require prevention of static charge may be applied.

[0117] In one example, the electronic substrate may be an OLED (Organic Light Emitting Diode) panel. Thus, in this case, the laminate may be an OLED device including an OLED panel and a pressure sensitive adhesive attached to one or both sides of the OLED panel.

[0118] Beneficial Effects

[0119] The present application can provide a polymer, a pressure-sensitive adhesive containing the polymer, a method for producing the polymer, and the use of the polymer or the pressure-sensitive adhesive. The present application can provide a polymer capable of forming a material having an excellent antistatic function and a method for producing the polymer, as well as the use of the polymer. The present application can provide such a polymer, a method for producing the polymer, and the use of the polymer, which can exhibit an antistatic function without adding a separate antistatic agent, does not ooze out components that exert an antistatic function, is easy to store, and can maintain the performance of the pressure-sensitive adhesive after being applied to the relevant pressure-sensitive adhesive, etc. BRIEF DESCRIPTION OF THE DRAWINGS

[0120] Figures 1 to 3 The NMR analysis results of the polymers prepared in the preparation examples are shown in FIG. DETAILED DESCRIPTION

[0121] Hereinafter, the present application will be described in detail through examples, but the scope of the present application is not limited by the following examples.

[0122] 1. Polymer structure, components and component ratio analysis methods

[0123] The structure, components and component ratio of the polymer were analyzed by HR-MAS (high resolution magic angle spinning) 1H NMR, 1H-13C HSQC (Heteronuclear Single Quantum Coherence) NMR and 1H-1H COSY (Correlation Spectroscopy) NMR.

[0124] 2. Surface resistance measurement

[0125] The surface resistance of the pressure-sensitive adhesive layer was measured under the conditions of a temperature of 25° C. and a relative humidity of 40%. After applying a voltage of 500 V for 10 seconds at the above temperature and relative humidity, the surface resistance was measured using HIRESTA-UP (MCP-HT450) of Mitsubishi Chemical.

[0126] 3. Evaluation of pollution resistance

[0127] After measuring the surface resistance, the contamination resistance was evaluated by visually observing the surface condition of the pressure-sensitive adhesive layer to determine whether contamination due to static electricity occurred in the pressure-sensitive adhesive layer.

[0128] The evaluation criteria for stain resistance are as follows.

[0129] <Evaluation criteria for stain resistance>

[0130] O: Determine that there is no contamination on the surface of the pressure-sensitive adhesive layer

[0131] X: Determine that there is contamination on the surface of the pressure-sensitive adhesive layer

[0132] 4. Evaluation of reprocessability

[0133] The reprocessability is evaluated by attaching the pressure-sensitive adhesive layer to the adherend, then peeling it off, and observing the surface condition of the peeled pressure-sensitive adhesive layer. Here, a glass substrate is used as the adherend, and peeling is performed at a peeling angle of about 180 degrees and a peeling rate of about 300 mm / minute.

[0134] The evaluation criteria for reprocessability are as follows.

[0135] <Evaluation criteria for reprocessability>

[0136] O: Determine that there is no pressure-sensitive adhesive residue on the surface of the adherend

[0137] Δ: There is a part of the pressure-sensitive adhesive residue on the surface of the adherend, making it slightly blurred

[0138] X: There is a large amount of pressure-sensitive adhesive residue on the surface of the adherend, making it blurred.

[0139] 5. GPC (Gel Permeation Chromatography)

[0140] The molecular weight is measured using GPC (Gel Permeation Chromatography). The polymer is placed in a 5 mL vial and diluted to a concentration of about 1 mg / mL in THF (tetrahydrofuran). Thereafter, the standard sample for calibration and the sample to be analyzed are filtered through a syringe filter (pore size: 0.45 μm), and then measured. As the analysis program, ChemStation of Agilent technologies is used, and the weight-average molecular weight (Mw) is obtained by comparing the elution time of the sample with the calibration curve.

[0141] <GPC measurement conditions>

[0142] Instrument: 1200 series of Agilent technologies

[0143] Column: Two PLgel mixed B from Polymer laboratories are used

[0144] Solvent: THF

[0145] Column temperature: 35 °C

[0146] Sample concentration: 1 mg / mL, 200 μL injection

[0147] Standard sample: polystyrene (Mp: 3900000, 723000, 316500, 52200, 31400, 7200, 3940, 485).

[0148] Preparation Example 1. Preparation of polymer (A)

[0149] Into a 1L reactor in which nitrogen is refluxed and a cooling device is installed to facilitate temperature regulation, 2-ethylhexyl acrylate (EHA), N-vinyl-2-pyrrolidone (NVP), methyl methacrylate (MMA), 2-hydroxyethyl acrylate (HEA) and 2-(dimethylamino)ethyl acrylate (DMAEA) are introduced in a weight ratio of 72:5:10:10:3 (EHA:NVP:MMA:HEA:DMAEA), and ethyl acetate (EAc) is introduced as a solvent. The solvent is introduced in an amount of about 50 to 60 parts by weight relative to 100 parts by weight of all monomers. Subsequently, nitrogen is purged to remove oxygen, and then a reaction initiator (AIBN, azobisisobutyronitrile) is introduced at a temperature of 65°C to initiate the reaction. The reaction initiator is introduced in an amount of about 400ppm or so. The reaction is carried out until a time point when the monomer conversion rate is about 90% or more to obtain a primary polymer (primary polymerization product).

[0150] Here, the conversion rate is obtained according to the following Equation 1.

[0151] [Equation 1]

[0152] Conversion rate (%) = 100 × (C / B) / A

[0153] 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.

[0154] 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 of the primary polymer before drying (B) is the weight of the polymer measured after polymerizing the mixture including the solvent and the monomer.

[0155] In Equation 1, the polymer is dried by maintaining it at a temperature of about 150° C. for about 30 minutes to obtain the weight (C).

[0156] Ethyl bromide was introduced into the primary polymer. Ethyl bromide was introduced in an amount of 1 equivalent relative to the 2-(dimethylamino)ethyl acrylate (DMAEA) unit contained in the polymer. Ethyl bromide was introduced, and the reaction was performed at 80° C. for another 20 hours to obtain the target polymer (A).

[0157] The weight average molecular weight (Mw) of the obtained polymer (A) is about 200,000.

[0158] Figure 1 It is a graph showing the results of NMR analysis of polymer (A).

[0159] pass Figure 1 , it can be determined that the 2-(dimethylamino)ethyl acrylate (DMAEA) unit is converted into a unit of the following formula A by reaction with ethyl bromide.

[0160] [Formula A]

[0161]

[0162] In formula A, R is hydrogen, L is ethylene, R1 and R3 are methyl, and R2 is ethyl.

[0163] Table 1 shows the results of determining the weight ratios of polymerization units contained in the polymer during the above manufacturing process, and EHA, MMA, NVP, HEA, DMAEA and formula A are ratios of 2-ethylhexyl acrylate, N-vinyl-2-pyrrolidone, methyl methacrylate, 2-hydroxyethyl acrylate, 2-(dimethylamino)ethyl acrylate and the unit of the above formula A, respectively.

[0164] [Table 1]

[0165] EHA MMA NVP HEA DMAEA Formula A Primary polymer 67.6 11.8 5.3 12.0 3.4 Polymer (A) 68.9 10.9 4.7 12.3 3.3

[0166] Preparation Example 2. Preparation of polymer (B)

[0167] A primary polymer was prepared in the same manner as in Preparation Example 1, except that when preparing the primary polymer, the monomer ratio was changed to a weight ratio of 70:5:10:10:5 (EHA:NVP:MMA:HEA:DMAEA), and 1 equivalent of ethyl bromide was introduced into the obtained primary polymer compared to 2-(dimethylamino)ethyl acrylate (DMAEA) contained in the polymer, and the reaction was performed at a temperature of 80° C. for additional 20 hours to obtain the target polymer (B).

[0168] The weight average molecular weight (Mw) of the obtained polymer (B) is about 200,000.

[0169] Figure 2: is a graph showing the NMR analysis results of the polymer (B), wherein the left side is the result of the primary polymer, and the right side is the result of the final polymer (B).

[0170] pass Figure 2 From the peak shifts in the left and right figures of , it can be determined that the 2-(dimethylamino)ethyl acrylate (DMAEA) unit is converted into the unit of the above formula A by reacting with ethyl bromide.

[0171] Table 2 shows the results of determining the weight ratios of the polymerized units contained in the polymer during the above manufacturing process, and EHA, MMA, NVP, HEA, DMAEA and formula A are ratios of 2-ethylhexyl acrylate, N-vinyl-2-pyrrolidone, methyl methacrylate, 2-hydroxyethyl acrylate, 2-(dimethylamino)ethyl acrylate and the unit of the above formula A, respectively.

[0172] [Table 2]

[0173] EHA MMA NVP HEA DMAEA Formula A Primary polymer 64.8 12.6 4.9 12.3 5.4 Polymer (B) 63.1 11.7 5.2 14.9 5.2

[0174] Preparation Example 3. Preparation of polymer (C)

[0175] A primary polymer was prepared in the same manner as in Preparation Example 1, except that when preparing the primary polymer, the monomer ratio was changed to a weight ratio of 65:5:10:10:10 (EHA:NVP:MMA:HEA:DMAEA), and 1 equivalent of ethyl bromide was introduced into the obtained primary polymer compared to 2-(dimethylamino)ethyl acrylate (DMAEA) contained in the polymer, and the reaction was performed at a temperature of 80° C. for additional 20 hours to obtain the target polymer (C).

[0176] The weight average molecular weight (Mw) of the obtained polymer (C) is about 200,000.

[0177] Figure 3 It is a graph showing the results of NMR analysis of polymer (C).

[0178] pass Figure 3 , it can be determined that the 2-(dimethylamino)ethyl acrylate (DMAEA) unit is converted into the unit of the above formula A by reaction with ethyl bromide.

[0179] The following Table 3 shows the results of determining the weight ratios of polymerized units contained in the polymer during the manufacturing process, wherein EHA, MMA, NVP, HEA, DMAEA and Formula A are ratios of 2-ethylhexyl acrylate, N-vinyl-2-pyrrolidone, methyl methacrylate, 2-hydroxyethyl acrylate, 2-(dimethylamino)ethyl acrylate and the unit of the above Formula A, respectively.

[0180] [Table 3]

[0181] EHA MMA NVP HEA DMAEA Formula A Primary polymer 63.8 10.2 4.8 11.3 9.9 Polymer (C) 60.4 10.1 5.2 14.2 10.2

[0182] Preparation Example 4. Preparation of polymer (D)

[0183] Into a 1L reactor in which nitrogen was refluxed and a cooling device was installed to facilitate temperature regulation, 2-ethylhexyl acrylate (EHA), N-vinyl-2-pyrrolidone (NVP), methyl methacrylate (MMA) and 2-hydroxyethyl acrylate (HEA) were introduced at a weight ratio of 75:5:10:10 (EHA:NVP:MMA:HEA), and ethyl acetate (EAc) was introduced as a solvent. Subsequently, nitrogen was purged to remove oxygen, and then azobisisobutyronitrile (AIBN) was introduced as a reaction initiator at a temperature of 65°C to initiate the reaction.

[0184] The reaction was carried out until the time point when the conversion rate was about 90% to obtain the target polymer (D). The method of measuring the conversion rate was the same as in the above Preparation Example 1. The weight average molecular weight (Mw) of the polymer (D) was about 200,000.

[0185] Preparation Example 5. Preparation of polymer (E)

[0186] Polymer (E) was prepared in the same manner as in Preparation Example 4, except that 2-ethylhexyl acrylate (EHA), N-vinyl-2-pyrrolidone (NVP) and 2-hydroxyethyl acrylate (HEA) were introduced into the reactor at a weight ratio of 85:5:10 (EHA:NVP:HEA). The weight average molecular weight (Mw) of polymer (E) was about 200,000.

[0187] Preparation Example 6. Preparation of polymer (F)

[0188] Polymer (F) was prepared in the same manner as in Preparation Example 4, except that 2-ethylhexyl acrylate (EHA), methyl methacrylate (MMA) and 2-hydroxyethyl acrylate (HEA) were introduced into the reactor at a weight ratio of 80:10:10 (EHA:NVP:HEA). The weight average molecular weight (Mw) of polymer (F) was about 200,000.

[0189] Example 1

[0190] About 0.25 parts by weight of a crosslinking agent (DR-7030HD, Samyoung Ink) and about 3 parts by weight of acetylacetone were added to the polymer (A) of Preparation Example 1 relative to 100 parts by weight of the solid content of the polymer (A), diluted to an appropriate concentration, and uniformly mixed to prepare a pressure-sensitive adhesive composition. Subsequently, the pressure-sensitive adhesive composition was coated on a release paper and maintained 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.

[0191] Example 2

[0192] A pressure-sensitive adhesive layer was prepared 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.

[0193] Example 3

[0194] A pressure-sensitive adhesive layer was prepared 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.

[0195] Comparative Example 1

[0196] About 0.25 parts by weight of a crosslinking agent (DR-7030HD, Samyoung Ink), about 3 parts by weight of acetylacetone, and about 0.05 parts by weight of a lithium salt (lithium bis(trifluoromethanesulfonyl)imide) were added to the polymer (D) of Preparation Example 4 relative to 100 parts by weight of the solid content of the polymer (D), diluted to an appropriate concentration, and uniformly mixed to prepare a pressure-sensitive adhesive composition. Subsequently, the pressure-sensitive adhesive composition was coated on a release paper and maintained 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.

[0197] A pressure-sensitive adhesive layer was formed in the same manner as in Example 1 using the pressure-sensitive adhesive composition.

[0198] Comparative Example 2

[0199] 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 formulated amount of the lithium salt was changed to about 0.15 parts by weight relative to 100 parts by weight of the polymer.

[0200] Comparative Example 3

[0201] About 0.25 parts by weight of a crosslinking agent (DR-7030HD, Samyoung Ink), about 3 parts by weight of acetylacetone, and about 0.15 parts by weight of a lithium salt (lithium bis(trifluoromethanesulfonyl)imide) were added to the polymer (E) of Preparation Example 5 relative to 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. Subsequently, the pressure-sensitive adhesive composition was coated on a release paper and maintained 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.

[0202] A pressure-sensitive adhesive layer was formed in the same manner as in Example 1 using the pressure-sensitive adhesive composition.

[0203] Comparative Example 4

[0204] 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.

[0205] The evaluation results of the above Examples and Comparative Examples are summarized and described in Table 4 below.

[0206] [Table 4]

[0207] Example 1 Example 2 Example 3 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Surface resistance (Ω / □) <![CDATA[2.84×10 12 ]]> <![CDATA[1.02×10 12 ]]> <![CDATA[5.00×10 11 ]]> <![CDATA[6.51×10 13 ]]> <![CDATA[7.04×10 12 ]]> <![CDATA[7.83×10 12 ]]> <![CDATA[7.32×10 12 ]]> Pollution resistance O O O X O X O Reprocessability O O O Δ X Δ Δ

Claims

1. A polymer comprising an alkyl (meth)acrylate unit and a unit of the following formula 1: [Formula 1] in, 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. 2 . The polymer according to claim 1 , comprising the alkyl (meth)acrylate unit in an amount of 60 to 90 wt %.

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

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

5. The polymer according to claim 1, wherein L in Formula 1 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 R1 to R3 are each independently an alkyl group having 1 to 4 carbon atoms. 6 . The polymer according to claim 1 , comprising 1 to 30 parts by weight of the unit of Formula 1 relative to 100 parts by weight of the alkyl (meth)acrylate unit.

7. The polymer according to claim 1, further comprising a unit of the following formula 2: [Formula 2] in, 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.

8. The polymer according to claim 7, wherein in Formula 2, 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. 9 . The polymer according to claim 7 , comprising 0.5 to 20 parts by weight of the unit of Formula 2 relative to 100 parts by weight of the alkyl (meth)acrylate unit.

10. The polymer according to claim 1, further comprising a polar group-containing unit. 11 . The polymer according to claim 10 , comprising 1 to 30 parts by weight of the polar group-containing unit relative to 100 parts by weight of the alkyl (meth)acrylate unit.

12. A method for producing a polymer comprising the steps of: reacting a monomer mixture including an alkyl (meth)acrylate and a compound of the following Formula 3 to obtain a polymer; and The polymer is reacted with an alkyl halide: [Formula 3] Wherein, L1 is an alkylene group or an alkylidene group, R 12 is a hydrogen atom or an alkyl group, and R 10 and R 11 Each is 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 according to claim 1.

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

16. The pressure-sensitive adhesive according to claim 14, further comprising a pressure-sensitive adhesive agent that crosslinks the polymer, and a crosslinking inhibitor.

17. The pressure-sensitive adhesive according to claim 16, wherein the crosslinking agent is contained in a ratio of 0.01 to 10 parts by weight relative to 100 parts by weight of the polymer, the crosslinking inhibitor is contained in an amount of 0.1 to 10 parts by weight relative to 100 parts by weight of the polymer, and the ratio (A / B) of the weight of the crosslinking inhibitor (A) to the weight of the crosslinking agent (B) is in the range of 0.5 to 30. 18 . The pressure sensitive adhesive of claim 14 , wherein the weight average molecular weight of the polymer is in the range of 10,000 g / mol to 200,000 g / mol.

19. A laminate comprising: Electronic substrate; as well as A pressure sensitive adhesive according to claim 14 attached to one or both sides of the electronic substrate.

20. An OLED device, comprising: OLED panel; as well as The pressure sensitive adhesive according to claim 14 attached to one or both sides of the OLED panel.

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