KR20170037071A - Pressure-sensitive adhesive composition - Google Patents
Pressure-sensitive adhesive composition Download PDFInfo
- Publication number
- KR20170037071A KR20170037071A KR1020150136151A KR20150136151A KR20170037071A KR 20170037071 A KR20170037071 A KR 20170037071A KR 1020150136151 A KR1020150136151 A KR 1020150136151A KR 20150136151 A KR20150136151 A KR 20150136151A KR 20170037071 A KR20170037071 A KR 20170037071A
- Authority
- KR
- South Korea
- Prior art keywords
- pressure
- sensitive adhesive
- group
- adhesive composition
- weight
- Prior art date
Links
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 93
- 239000000203 mixture Substances 0.000 title claims abstract description 69
- 239000002313 adhesive film Substances 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims description 62
- 229920000642 polymer Polymers 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 25
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 22
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 19
- -1 4-vinyloxybutyl Chemical group 0.000 claims description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
- 239000010410 layer Substances 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 15
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 239000000853 adhesive Substances 0.000 claims description 9
- 230000001070 adhesive effect Effects 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000000962 organic group Chemical group 0.000 claims description 7
- 239000007983 Tris buffer Substances 0.000 claims description 6
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 4
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 claims description 4
- UEIPWOFSKAZYJO-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-[2-(2-ethenoxyethoxy)ethoxy]ethane Chemical compound C=COCCOCCOCCOCCOC=C UEIPWOFSKAZYJO-UHFFFAOYSA-N 0.000 claims description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000005591 trimellitate group Chemical group 0.000 claims description 4
- GPHWXFINOWXMDN-UHFFFAOYSA-N 1,1-bis(ethenoxy)hexane Chemical compound CCCCCC(OC=C)OC=C GPHWXFINOWXMDN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 239000011148 porous material Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 claims description 2
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 claims description 2
- AITKNDQVEUUYHE-UHFFFAOYSA-N 1,3-bis(ethenoxy)-2,2-dimethylpropane Chemical compound C=COCC(C)(C)COC=C AITKNDQVEUUYHE-UHFFFAOYSA-N 0.000 claims description 2
- CGHMMUAOPPRRMX-UHFFFAOYSA-N 1,4-bis(ethenoxy)cyclohexane Chemical compound C=COC1CCC(OC=C)CC1 CGHMMUAOPPRRMX-UHFFFAOYSA-N 0.000 claims description 2
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 claims description 2
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 claims description 2
- SUFSXWBMZQUYOC-UHFFFAOYSA-N 2,2-bis(ethenoxymethyl)propane-1,3-diol Chemical compound C=COCC(CO)(CO)COC=C SUFSXWBMZQUYOC-UHFFFAOYSA-N 0.000 claims description 2
- BXYWKXBAMJYTKP-UHFFFAOYSA-N 2-[2-[2-[2-(3-sulfanylpropanoyloxy)ethoxy]ethoxy]ethoxy]ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOCCOCCOCCOC(=O)CCS BXYWKXBAMJYTKP-UHFFFAOYSA-N 0.000 claims description 2
- ILRVMZXWYVQUMN-UHFFFAOYSA-N 3-ethenoxy-2,2-bis(ethenoxymethyl)propan-1-ol Chemical compound C=COCC(CO)(COC=C)COC=C ILRVMZXWYVQUMN-UHFFFAOYSA-N 0.000 claims description 2
- LABQKWYHWCYABU-UHFFFAOYSA-N 4-(3-sulfanylbutanoyloxy)butyl 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCCCCOC(=O)CC(C)S LABQKWYHWCYABU-UHFFFAOYSA-N 0.000 claims description 2
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 claims description 2
- YAAUVJUJVBJRSQ-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2-[[3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propoxy]methyl]-2-(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS YAAUVJUJVBJRSQ-UHFFFAOYSA-N 0.000 claims description 2
- HMNFSPVCKZFHGZ-UHFFFAOYSA-N bis(4-ethenoxybutyl) benzene-1,4-dicarboxylate Chemical compound C=COCCCCOC(=O)C1=CC=C(C(=O)OCCCCOC=C)C=C1 HMNFSPVCKZFHGZ-UHFFFAOYSA-N 0.000 claims description 2
- JZQAAQZDDMEFGZ-UHFFFAOYSA-N bis(ethenyl) hexanedioate Chemical compound C=COC(=O)CCCCC(=O)OC=C JZQAAQZDDMEFGZ-UHFFFAOYSA-N 0.000 claims description 2
- SDNBHBGJJPWRJG-UHFFFAOYSA-N bis[[4-(ethenoxymethyl)cyclohexyl]methyl] pentanedioate Chemical compound C1CC(COC=C)CCC1COC(=O)CCCC(=O)OCC1CCC(COC=C)CC1 SDNBHBGJJPWRJG-UHFFFAOYSA-N 0.000 claims description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 229960000834 vinyl ether Drugs 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- 239000012790 adhesive layer Substances 0.000 claims 1
- OLLMEZGFCPWTGD-UHFFFAOYSA-N hexane;methanol Chemical compound OC.OC.CCCCCC OLLMEZGFCPWTGD-UHFFFAOYSA-N 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 5
- 239000001301 oxygen Substances 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 230000000903 blocking effect Effects 0.000 abstract description 3
- 239000010408 film Substances 0.000 description 50
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 125000000524 functional group Chemical group 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 11
- 238000004132 cross linking Methods 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 230000004888 barrier function Effects 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
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- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
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- 235000019382 gum benzoic Nutrition 0.000 description 2
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- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- RLUFBDIRFJGKLY-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Cl RLUFBDIRFJGKLY-UHFFFAOYSA-N 0.000 description 1
- HIYIGPVBMDKPCR-UHFFFAOYSA-N 1,1-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1(COC=C)CCCCC1 HIYIGPVBMDKPCR-UHFFFAOYSA-N 0.000 description 1
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- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J123/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
- C09J123/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
- C09J123/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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- C09J7/02—
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Abstract
The present application provides a pressure-sensitive adhesive composition capable of effectively blocking water or oxygen introduced into the organic electronic device from the outside and capable of realizing not only durability reliability under harsh conditions such as high temperature and high humidity but also excellent optical characteristics and an adhesive film comprising the same .
Description
The present application relates to a pressure-sensitive adhesive composition, an adhesive film comprising the same, and an organic electronic device including the same.
An organic electronic device (OED) refers to an apparatus that includes an organic material layer that generates holes and electrons to generate an alternating current. Examples thereof include a photovoltaic device, a rectifier, A transmitter and an organic light emitting diode (OLED).
Organic light emitting diodes (OLEDs) among the organic electronic devices have lower power consumption, faster response speed, and are advantageous for thinning display devices or illumination. In addition, OLEDs are expected to be applied in various fields covering various portable devices, monitors, notebooks, and televisions because of their excellent space utilization.
In commercialization of OLEDs and expansion of applications, the main problem is durability. Organic materials and metal electrodes contained in OLEDs are very easily oxidized by external factors such as moisture. Thus, products containing OLEDs are highly sensitive to environmental factors. Accordingly, various methods have been proposed to effectively block penetration of oxygen or moisture from the outside into organic electronic devices such as OLEDs.
Patent Document 1 is a film of an adhesive encapsulating composition and an organic electroluminescent device, which is an adhesive based on PIB (polyisobutylene) and has poor processability and poor reliability under high temperature and high humidity conditions.
Therefore, it is required to develop an encapsulant that can maintain the reliability at high temperature and high humidity conditions and has excellent optical characteristics, while securing the required lifetime in the organic electronic device and effectively blocking the penetration of moisture.
The present application provides a pressure-sensitive adhesive composition which can effectively block moisture or oxygen introduced into the organic electronic device from the outside and has excellent mechanical properties such as handling and workability and transparency, and an adhesive film containing the same.
The present application relates to a pressure-sensitive adhesive composition. The pressure-sensitive adhesive composition can be applied to encapsulating or encapsulating organic electronic devices such as, for example, OLEDs. For example, the pressure-sensitive adhesive composition may be applied to encapsulate the front surface of an organic electronic device, or may be applied to a surface of the substrate on which the device is formed, to be located on the opposite side of the surface on which the device is formed.
As used herein, the term " organic electronic device " refers to an article or apparatus having a structure including an organic material layer that generates alternating electric charges using holes and electrons between a pair of electrodes facing each other, But are not limited to, photovoltaic devices, rectifiers, transmitters, and organic light emitting diodes (OLEDs). In one example of the present invention, the organic electronic device may be an OLED.
In this application, the pressure-sensitive adhesive composition comprises a polymer derived from isobutylene; And a polyfunctional compound including a vinyl ether group and / or a mercapto group. The polyfunctional compound may include at least one functional group selected from the group consisting of a vinyl ether group and a mercapto group. For example, the polyfunctional compound may include a vinyl ether group or may include a mercapto group. Alternatively, the pressure-sensitive adhesive composition of the present application may contain a polyfunctional compound having a functional group of a vinyl ether group and a polyfunctional compound having a functional group of a mercapto group. At least one of the polyfunctional compounds may have a cyclic structure in which the ring-constituting atoms within the molecular structure are in the range of 3 to 10, 4 to 9, or 5 to 8. In one example, the present application allows the compound to retain at least one or more of the annular structures after the adhesive is cured. In addition, the polyfunctional compound may not contain an acryloyl group or a methacryloyl group. In the present application, by using a compound having a specific functional group as the polyfunctional compound, shrinkage and the like of the pressure-sensitive adhesive can be prevented and excellent crosslinking density and the like can be realized.
The term " polymer derived from isobutylene " in the present application means that at least one of the polymerized units of the polymer is composed of isobutylene. Since the polymer derived from isobutylene has a very low polarity, is transparent, and has almost no effect of corrosion, excellent moisture barrier properties, endurance reliability and optical characteristics can be realized when used as an encapsulating material.
Also in the present application the polymer derived from isobutylene is a homopolymer of isobutylene monomer; A copolymer obtained by copolymerizing an isobutylene monomer with another monomer capable of polymerization; Or a mixture thereof. The polymers derived from this application may mean that the monomers are forming polymers in polymerized units.
Other monomers polymerizable with the isobutylene monomer may include, for example, 1-butene, 2-butene, isoprene, styrene or butadiene. By using the copolymer, physical properties such as processability and degree of crosslinking can be maintained, and occurrence of dark spots due to electrochemical corrosion can be minimized when applied to organic electronic devices.
In one example, the polymer is selected from the group consisting of polyisobutylene, a copolymer of isobutylene and isoprene, a copolymer of isoprene and styrene, a copolymer of isobutylene and styrene, a copolymer of butadiene and styrene, a copolymer of isoprene, Copolymers of isoprene and styrene, copolymers of butadiene and styrene, or copolymers of isoprene, butadiene and styrene can be exemplified.
In addition, the polymer may have at least one reactive functional group. The reactive functional group may be a form in which a monomer having a reactive functional group is grafted onto the polymer, but is not limited thereto. That is, in this case, the polymer may be a copolymer in which the monomer is grafted to a polymer derived from isobutylene to be modified. Examples of the reactive functional group may be a cyclic epoxide group, a glycidyl ether group, a hydroxyl group, a carboxyl group, an amine group or an anhydride group, and the monomer having a reactive functional group may be a compound having a vinyl group or a (meth) Lt; / RTI > Further, in one example, the reactive functional group may be introduced via epoxidation into an unsaturated group in the polymer.
In the present application, the polymer may have a weight average molecular weight (MW) such that the pressure-sensitive adhesive composition can be formed into a film. For example, the polymer may have a weight average molecular weight of about 100,000 to 2,000,000, 100,000 to 1,500,000, or 100,000 to 1,000,000. The term "weight average molecular weight" as used herein means a value converted to a standard polystyrene measured by GPC (Gel Permeation Chromatograph). However, the resin component does not necessarily have to have the weight average molecular weight mentioned above. For example, even when the molecular weight of the resin component does not become so high as to form a film, a separate binder resin may be blended into the pressure-sensitive adhesive composition. The term polymer and resin component may be used interchangeably herein.
As described above, the pressure-sensitive adhesive composition may include a polyfunctional compound including a vinyl ether group or a mercapto group together with a polymer derived from isobutylene.
In the present application, the polyfunctional compound has high compatibility with a polymer derived from isobutylene, and can form a specific crosslinked structure together with the polymer. For example, the polyfunctional compound may mean a compound containing two or more functional groups such as a functional group capable of participating in the polymerization reaction by irradiation with an active energy ray, for example, a vinyl ether group or a mercapto group. The crosslinked structure may be a crosslinked structure formed by application of heat, a crosslinked structure formed by irradiation of an active energy ray, or a crosslinked structure formed by aging at room temperature. In the above, the term " active energy ray " includes microwaves. Particles such as alpha-particle beam, proton beam, neutron beam or electron beam as well as infrared (IR), ultraviolet (UV), X-ray and gamma rays Beam, etc., and may be typically ultraviolet or electron beam.
The polyfunctional compound containing the vinyl ether group may satisfy the following formula (1).
[Chemical Formula 1]
In Formula 1, R 1 may be an organic group. Also, X may be a single bond, or a straight chain or branched alkylene group having 1 to 12 carbon atoms, 1 to 8, 1 to 6, or 1 to 4 carbon atoms. In addition, n may be an integer of 2 to 8. When the pressure-sensitive adhesive composition according to the present invention includes a polyfunctional compound having a specific structure as described above, when the pressure-sensitive adhesive having a crosslinked structure is applied as an encapsulating material, excellent crosslinking density can be formed and heat resistance and durability of the pressure-sensitive adhesive can be realized.
In one example, the compound of Formula 1 is selected from the group consisting of bis (4- (vinyloxymethyl) cyclohexylmethyl) glutarate, tri (ethylene glycol) divinyl ether, adipic acid divinyl ester, diethylene glycol divinyl ether, Tris (4-vinyloxybutyl) trimellitate, 1,3,5-tris (4-vinyloxybutyl) trimellitate, bis (4- (vinyloxy) butyl) terephthalate, bis Ethylene glycol divinyl ether, 1,4-butanediol divinyl ether, tetramethylene glycol divinyl ether, tetraethylene glycol divinyl ether, neopentyl glycol divinyl ether, trimethylol (trimethylolpropane) divinyl ether, Hexanediol divinyl ether, 1,4-cyclohexanediol divinyl ether, tetraethylene glycol divinyl ether, pentaerythritol divinyl ether, pentaerythritol trivinyl ether, or 1, 2-pentanediol divinyl ether. 4 o'clock Cyclohexanedimethanol divinyl ether, and the like, but are not limited thereto.
The polyfunctional compound containing the vinyl ether group may be used in an amount of 10 to 100 parts by weight, 20 to 90 parts by weight, 30 to 80 parts by weight, 40 to 80 parts by weight, 43 to 77 parts by weight, 46 to 74 parts by weight or 49 to 71 parts by weight. By controlling the content of the polyfunctional compound containing a vinyl ether group in the above content range, the present application can improve transparency by improving compatibility with a resin component, and can realize excellent durability and the like.
Further, in one embodiment of the present invention, the multifunctional compound containing the mercapto group may satisfy the following general formula (2).
(2)
In the general formula (2), R 2 represents an organic group, and Y represents a single bond or -COO-. Further, Z may be a straight chain or branched alkylene group having 1 to 12 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms. In addition, n may represent an integer of 2 to 8. When the pressure-sensitive adhesive composition according to the present invention includes a polyfunctional compound having a specific structure as described above, when the pressure-sensitive adhesive having a crosslinked structure is applied as an encapsulating material, excellent crosslinking density can be formed and heat resistance and durability of the pressure-sensitive adhesive can be realized.
In one example, the compound of Formula 2 is selected from the group consisting of 2-mercaptobenzothiazole, 1,4-bis (3-mercaptobutyryloxy) butane, 1,3,5-tris (3-mercaptobutyloxy Ethyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -thione, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis Mercaptobutylate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexakis (3-mercaptopropionate) or tetraethylene glycol bis (3-mercaptopropionate) And the like, but the present invention is not limited thereto.
The multifunctional compound containing the mercapto group may be used in an amount of 1 to 50 parts by weight, 3 to 40 parts by weight, 5 to 30 parts by weight, 8 to 25 parts by weight or 9 to 20 parts by weight based on 100 parts by weight of the polymer derived from isobutylene ≪ / RTI > By controlling the content of the multifunctional compound containing a mercapto group in the content range described above, transparency can be easily secured by improving compatibility with a resin component, and durability and the like can be excellently realized.
In the present specification, an organic group may mean a functional group composed of an organic compound, and examples thereof include an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkoxycarbonyl group, a cyano group or a nitro group. The organic group may have a cyclic structure in which the ring-constituting atoms within the molecular structure are in the range of 3 to 10, 4 to 9, or 5 to 8. Examples of the cyclic structure include, but are not limited to, the following cycloalkyl groups and the like. When the polyfunctional compound of the present application has a cyclic structure in the molecular structure, the pressure-sensitive adhesive composition may be stable to external factors such as shrinkage and expansion even after curing.
The term alkyl group as used herein includes, unless otherwise specified, a linear or branched 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 a linear or branched alkyl group having 3 to 20 carbon atoms, Or a cycloalkyl group having 3 to 16 carbon atoms or 4 to 12 carbon atoms. The alkyl group may be optionally substituted with one or more substituents.
As used herein, unless otherwise specified, the term alkoxy group may mean an alkoxy 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. The alkoxy group may be linear, branched or cyclic. In addition, the alkoxy group may be optionally substituted with one or more substituents.
In the present specification, the term alkylene group or alkylidene group may mean an alkylene group or alkylidene group having 1 to 12 carbon atoms, 4 to 10 carbon atoms, or 6 to 9 carbon atoms unless otherwise specified. The alkylene group or alkylidene group may be linear, branched or cyclic. Also, the alkylene group or alkylidene group may be optionally substituted with one or more substituents.
The alkenyl group in the present specification may mean an alkenyl group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms unless otherwise specified. The alkenyl group may be linear, branched or cyclic. In addition, the alkenyl group may be optionally substituted with one or more substituents.
In one example, R 1 or R 2 in the above formula (1) or (2) may be a residue derived from an alkyl group. A residue derived from an alkyl group may mean that it consists of an alkyl group as a residue of a specific compound. For example, in Formula 1, when n is 2, R 1 may be an alkylene group. When n is 3 or more, R 1 may be bonded to oxygen of Formula 1 by desorbing two or more hydrogen atoms of the alkyl group.
In addition, the pressure sensitive adhesive composition of the present invention may comprise a mixture of a polyfunctional compound containing a vinyl ether group and a polyfunctional compound containing a mercapto group.
In one example, the mixture of polyfunctional compounds is 30-90 parts by weight, 33-87 parts by weight, 36-84 parts by weight or 39-81 parts by weight or 42-78 parts by weight, based on 100 parts by weight of the polymer derived from isobutylene. May be included in parts by weight. The multifunctional compound containing a vinyl ether group and the multifunctional compound containing a mercapto group may be contained in a proportion of 30 to 80 parts by weight and 1 to 30 parts by weight, respectively. By controlling the content within the above range, the cross-linking density of the pressure-sensitive adhesive composition can be increased to realize excellent moisture resistance and durability reliability.
In the present application, the pressure-sensitive adhesive composition may further include a tackifier or a photoinitiator.
In one embodiment, the tackifier may be a hydrogenated cyclic olefinic polymer or a terpene phenolic resin. The tackifier may be a resin produced by reacting a terpene compound with an aromatic compound. When the tackifier has an aromatic group in the molecular structure, the compatibility between the polymer and the polyfunctional compound can be improved. The aromatic compound may include a reactive functional group. Examples of the functional group include a hydroxyl group, a carboxyl group, and an amine group. Specifically, the aromatic compound may be phenol, and the tackifier may be a terpene phenolic resin. Further, in one example, the present application can use a hydrogenated petroleum resin obtained by hydrogenating a petroleum resin as a tackifier. The hydrogenated petroleum resin may be partially or fully hydrogenated and may be a mixture of such resins. Such a tackifier can be selected to have good compatibility with the pressure-sensitive adhesive composition, excellent moisture barrier property, and low organic volatile components. Specific examples of the hydrogenated petroleum resins include hydrogenated terpene resins, hydrogenated ester resins, and hydrogenated dicyclopentadiene resins. The weight average molecular weight of the tackifier may be from about 200 to about 5,000. The content of the tackifier can be appropriately adjusted as needed. For example, the content of the tackifier may be selected in consideration of the compatibility with the resin component, etc. According to one example, 5 parts by weight to 100 parts by weight, 8 parts by weight to 100 parts by weight, 95 parts by weight, 10 parts by weight to 93 parts by weight or 15 parts by weight to 90 parts by weight.
In the present application, the pressure-sensitive adhesive composition may further comprise a radical initiator. The radical initiator may be a photo radical or a thermal radical initiator. The specific kind of the photoinitiator can be appropriately selected in consideration of the curing rate and the possibility of yellowing. For example, benzoin, hydroxy ketone, amino ketone or phosphine oxide photoinitiators can be used. Specific examples thereof include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether , Benzoin n-butyl ether, benzoin isobutyl ether, acetophenone, dimethyl anino acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy- 2-methyl-1-phenylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) (2-hydroxyethoxy) phenyl-2- (hydroxy-2-propyl) ketone, benzophenone, p-phenylbenzophenone, 4,4'- diethylaminobenzophenone, dichlorobenzophenone 2-methylanthraquinone, 2-ethyl anthraquinone, 2-t-butyl anthraquinone, 2-aminoanthraquinone, thioxanthone, 2-ethylthioxanthone, 2- 4-dimethylthi 2-methyl-11 [4- (1-methylvinyl) phenyl] benzoic acid, Propanone] and 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide can be used.
The content of the photo-radical initiator may be varied depending on the kind and ratio of the functional group of the radical-curable compound, each density to be implemented, and the like. For example, the photo radical initiator may be blended at a ratio of 0.1 part by weight to 20 parts by weight or 0.1 parts by weight to 15 parts by weight based on 100 parts by weight of the polyfunctional compound. The present invention can effectively control the reaction of the polyfunctional compound and prevent deterioration of the physical properties of the pressure-sensitive adhesive composition due to the remaining components after curing by controlling the content of the photo radical initiator in the above range.
The present application also relates to an adhesive film comprising a pressure-sensitive adhesive layer containing the pressure-sensitive adhesive composition.
The structure of the pressure-sensitive adhesive film of the present application is not particularly limited as long as it includes the above-described pressure-sensitive adhesive composition, and examples thereof include a base film or a release film (hereinafter, may be referred to as "first film"); And a pressure-sensitive adhesive layer formed on the base film or the release film.
The pressure-sensitive adhesive film of the present application may further include a base film or release film (hereinafter sometimes referred to as " second film ") formed on the pressure-sensitive adhesive composition.
The specific kind of the first film that can be used in the present application is not particularly limited. In the present application, for example, a general polymer film in this field can be used as the first film. In the present application, for example, the base material or the release film may be a polyethylene terephthalate film, a polytetrafluoroethylene film, a polyethylene film, a polypropylene film, a polybutene film, a polybutadiene film, a polyvinyl chloride film, , An ethylene-vinyl acetate film, an ethylene-propylene copolymer film, an ethylene-ethyl acrylate copolymer film, an ethylene-methyl acrylate copolymer film, or a polyimide film. In addition, a suitable mold release treatment may be performed on one or both surfaces of the base film or release film of the present application. Examples of the releasing agent used in the releasing treatment of the base film include an alkyd type, a silicone type, a fluorine type, an unsaturated ester type, a polyolefin type, a wax type and the like. Among them, the use of an alkyd type, a silicone type or a fluorine type releasing agent But is not limited thereto.
Also, the kind of the second film (hereinafter sometimes referred to as " cover film ") that can be used in the present application is not particularly limited either. For example, in the present application, as the second film, the same or a different kind as the first film may be used within the scope exemplified in the first film described above. In the present application, the second film may also be subjected to appropriate mold release treatment.
In one embodiment, the pressure-sensitive adhesive film of the present application may satisfy the following general formula (1).
[Formula 1]
DELTA X ≤ 1.2 mm
X in the general formula (1) is a value obtained when the substrate film formed on one surface of the pressure-sensitive adhesive layer having a thickness of 30 탆 is adhered to a glass plate with an adhesive area of 1 cm 2 and aged for 24 hours and then a load of 1.5 kg at 25 캜 is applied for 1000 seconds The pressure-sensitive adhesive film may satisfy the following general formula (2).
[Formula 2]
Gel content (% by weight) = B / A × 100 ≥ 30%
B represents the mass of the pressure-sensitive adhesive composition, B represents the mass of the pressure-sensitive adhesive composition obtained by immersing the pressure-sensitive adhesive composition in toluene at 25 DEG C for 24 hours, filtering it with a mesh of 200 mesh (pore size 74 mu m) Lt; RTI ID = 0.0 >% < / RTI > of the insoluble content of the pressure-sensitive adhesive composition. The pushing distance represented by the general formula 1 may be 1.2 mm or less, 0.1 to 1.1 mm, 0.15 to 1.0 mm, or 0.2 to 0.93 mm. That is, the present invention secures an appropriate range of the crosslinking structure and the degree of crosslinking, thereby controlling the pushing distance to 1.2 mm or less. In particular, when the adhesive film is applied to organic electronic devices, excellent moisture barrier properties, And optical characteristics.
In the general formula (2), A represents the mass of the pressure-sensitive adhesive, B represents the mass of the pressure-sensitive adhesive which is immersed in toluene at 25 ° C for 24 hours, and then is filtered through a mesh of 200 mesh (pore size 74 μm) It represents the dry weight of the insoluble component of the adhesive.
The gel content represented by the general formula 2 may be 20% to 70%, 25% to 65%, or 30% to 60%. That is, the present invention can provide a pressure-sensitive adhesive having excellent crosslinking structure and degree of crosslinking by controlling the gel content within the above range, and such pressure-sensitive adhesive can have excellent moisture barrier properties, durability and optical properties.
In one example, the adhesive film satisfying the above general formula (1) or (2) may have a moisture permeability of 4 mm or less. That is, the pressure-sensitive adhesive composition comprising the pressure-sensitive adhesive composition or the crosslinked product thereof according to the present invention satisfies the general formula 1 or 2 and can achieve excellent moisture barrier properties.
In one embodiment of the present application, the adhesive film may exhibit a haze increase of 10% or less, 9% or less, 8% or less, or 7% or less according to changes over time under uncured conditions. That is, the pressure-sensitive adhesive film comprising the pressure-sensitive adhesive composition or the crosslinked product according to the present application can have excellent light transmittance by using a polyfunctional compound having excellent compatibility with the resin component. The optical characteristics may be measured at 550 nm using a UV-Vis spectrometer.
The present application also includes a
In the present invention, the organic electronic device may be an organic light emitting diode.
The organic electronic device may further include a protective film for protecting the device on the organic electronic device.
The organic electronic device may further include a
The present application also relates to a method of manufacturing an organic electronic device, comprising the step of forming an adhesive film on the other side of a substrate on which an organic electronic element is formed, the adhesive film comprising the above-described adhesive composition. In one example, the manufacturing method may further include a step of crosslinking or curing the adhesive film.
In addition, the adhesive film exhibits excellent transparency and can be formed as a stable adhesive film regardless of the form of the organic electronic device such as top emission or bottom emission.
As used herein, the term " curing " means that the adhesive composition of the present invention forms a cross-linked structure through heating or UV irradiation, etc., and is produced in the form of a pressure-sensitive adhesive.
Specifically, a transparent electrode is formed on a glass or polymer film used as a substrate by a method such as vacuum deposition or sputtering. On the transparent electrode, a light-emitting organic material composed of a hole transporting layer, a light- And then an electrode layer is further formed on the electrode layer to form an organic electronic device.
Then, the adhesive film is placed on the other surface of the substrate, and the adhesive film is heated using a laminate or the like to press the adhesive film in a state of imparting fluidity, and the resin in the adhesive film can be crosslinked.
The present application provides a pressure-sensitive adhesive composition capable of effectively blocking water or oxygen introduced into the organic electronic device from the outside and capable of realizing not only durability reliability under harsh conditions such as high temperature and high humidity but also excellent optical characteristics and an adhesive film comprising the same .
1 is a cross-sectional view showing an organic electronic device according to one example of the present invention.
Hereinafter, the present invention will be described in more detail with reference to the following examples and comparative examples, but the scope of the present invention is not limited by the following examples.
One. Gel content
Gel content (% by weight) = B / A x 100
B represents the mass of the pressure-sensitive adhesive composition, B represents the mass of the pressure-sensitive adhesive composition which is not passed through the screen, B represents the mass of the pressure-sensitive adhesive composition which is not passed through the screen, B represents the mass of the pressure- Of the dry mass of the insoluble component of the solution.
2. Creep
Examples and a comparative example, a pressure-sensitive adhesive composition load of 1.5 kg at 25 ℃ was attached to a base film formed on one surface a pressure-sensitive adhesive layer having a thickness of 30 ㎛ the adhesion area 1cm 2 glass plate and stand for 24 hours, including walked for 1000 sec , The change in the pushing distance of the pressure-sensitive adhesive layer was measured between 50 seconds and 1000 seconds. The base film used was a polyethylene terephthalate (PET) film.
3. moisture permeability
A pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition of Examples and Comparative Examples was laminated on the face-sealing pressure-sensitive adhesive, and a barrier film (thickness: (FTB 3-50, 3M), cured by UV irradiation, aged at room temperature for 1 day, and then measured for penetration length on the basis of 500 hours at 85 ° C and 85% relative humidity.
Example One
10 g of polyisobutylene (Oppanol B80, manufactured by BASF) as a polymer was charged into a mixing vessel, and 1,4-cyclohexanedimethanol divinyl ether (Aldrich) as a polyfunctional compound containing a vinyl ether group was added to the solid content Was added to the vessel in an amount of 50 parts by weight based on 100 parts by weight. Further, pentaerythritoltetrakis (3-mercaptobutylate) (Showadenko) as a multifunctional compound containing a mercapto group was added in an amount of 10 parts by weight based on 100 parts by weight of the solid content of the polyfunctional compound containing a vinyl ether group (DERTOPHENE T 115, manufactured by DRT) was added to the container in an amount of 40 parts by weight based on 100 parts by weight of the polymer. A photoinitiator (Irgacure 184, Ciba Chemical) was added to the vessel in an amount of 5 parts by weight based on 100 parts by weight of the solid content of the polyfunctional compound containing the vinyl ether group. A homogeneous pressure-sensitive adhesive composition solution (solvent: toluene) was prepared using a conventional mechanical stirrer as the mixing container.
The prepared solution was coated on the releasing surface of the releasing PET and dried in an oven at 100 캜 for 15 minutes to prepare an adhesive film comprising a pressure-sensitive adhesive layer having a thickness of 30 탆. The properties of the produced film were measured on a sample irradiated with ultraviolet rays of 2 J / cm 2 .
Example 2
A pressure-sensitive adhesive composition and a pressure-sensitive adhesive film were prepared in the same manner as in Example 1 except that butyl rubber (RB301, manufactured by Lanxess) was used as a polymer.
Example 3
(SIBSTAR62M, manufactured by Kaneka) as a polymer and 70 parts by weight of a polyfunctional compound containing a vinyl ether group was added to 100 parts by weight of a solid content of the polymer, To prepare a pressure-sensitive adhesive composition and a pressure-sensitive adhesive film.
Comparative Example One
Example 1 was repeated except that triarylsulfonium hexafluoroantimonate (aldrich) was added as a photoinitiator in an amount of 3 parts by weight based on 100 parts by weight of the solid content of the polyfunctional compound containing a vinyl ether group without adding a multifunctional compound containing a mercapto group. The pressure-sensitive adhesive composition and the pressure-sensitive adhesive film were prepared in the same manner.
Comparative Example 2
The polyfunctional compound containing a vinyl ether group was changed to urethane diacrylate (PU2034, manufactured by Miwon), and the urethane acrylate content was added in an amount of 20 parts by weight based on 100 parts by weight of the solid content of the polymer. The multi- A pressure-sensitive adhesive composition and a pressure-sensitive adhesive film were prepared in the same manner as in Example 1, except that no compound was added.
Comparative Example 3
A polyfunctional compound containing a vinyl ether group was changed to pentaerythritol triacrylate (M420, Miwon), a polyfunctional compound containing a mercapto group was not added, and the pentaerythritol triacrylate content was changed from a solid content Sensitive adhesive composition and an adhesive film were prepared in the same manner as in Example 1, except that 10 parts by weight of water was used.
Comparative Example 4
A polyfunctional compound containing a vinyl ether group was changed to pentaerythritol triacrylate (M420, manufactured by Miwon) using a butyl rubber (RB301, manufactured by Lanxess) as a polymer, and a multifunctional compound containing a mercapto group was not added And the content of the pentaerythritol triacrylate was changed to 10 parts by weight with respect to 100 parts by weight of the solid content of the polymer, a pressure sensitive adhesive composition and a pressure sensitive adhesive film were prepared in the same manner as in Example 1.
The above measurement results are summarized in Table 1 below.
21: substrate
22: Cover substrate
23: Organic electronic device
24: Adhesive film
12: Encapsulation material
Claims (19)
[Chemical Formula 1]
Wherein R 1 represents an organic group, X represents a single bond or an alkylene group having 1 to 12 carbon atoms, and n represents an integer of 2 to 8.
(2)
In Formula 1, R 2 represents an organic group, Y represents a single bond or -COO-, Z represents an alkylene group having 1 to 12, n is an integer of 2 to 8.
[Formula 1]
DELTA X &le; 1.2 mm
X in the general formula (1) is a value obtained when the substrate film formed on one surface of the pressure-sensitive adhesive layer having a thickness of 30 탆 is adhered to a glass plate with an adhesive area of 1 cm 2 and aged for 24 hours and then a load of 1.5 kg at 25 캜 is applied for 1000 seconds Indicates the pushing distance of the pressure-sensitive adhesive layer.
[Formula 2]
Gel content (% by weight) = B / A × 100 ≥ 30%
B represents the mass of the pressure-sensitive adhesive composition, B represents the mass of the pressure-sensitive adhesive composition obtained by immersing the pressure-sensitive adhesive composition in toluene at 25 DEG C for 24 hours, filtering it with a mesh of 200 mesh (pore size 74 mu m) Lt; RTI ID = 0.0 >%< / RTI > of the insoluble content of the pressure-sensitive adhesive composition.
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Cited By (2)
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| JP2019014846A (en) * | 2017-07-10 | 2019-01-31 | 綜研化学株式会社 | Composition, adhesive and adhesive sheet |
| KR20200007245A (en) * | 2018-07-12 | 2020-01-22 | 율촌화학 주식회사 | Adhesive film and adhesive tape for moisture protection, and method for producing the same |
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| JP2008248055A (en) * | 2007-03-30 | 2008-10-16 | Kaneka Corp | Composition for sealing material, and sealing material |
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| JP2019014846A (en) * | 2017-07-10 | 2019-01-31 | 綜研化学株式会社 | Composition, adhesive and adhesive sheet |
| KR20200007245A (en) * | 2018-07-12 | 2020-01-22 | 율촌화학 주식회사 | Adhesive film and adhesive tape for moisture protection, and method for producing the same |
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| KR102041816B1 (en) | 2019-11-07 |
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