WO2022163281A1 - 活性エネルギー線硬化性粘着シート、離型フィルム付き粘着シート、積層体、積層体の製造方法、積層シート、画像表示装置用積層体、フレキシブル画像表示装置，フレキシブルディスプレイ用粘着シートおよび画像表示装置用積層体の製造方法 - Google Patents

活性エネルギー線硬化性粘着シート、離型フィルム付き粘着シート、積層体、積層体の製造方法、積層シート、画像表示装置用積層体、フレキシブル画像表示装置，フレキシブルディスプレイ用粘着シートおよび画像表示装置用積層体の製造方法 Download PDF

Info

Publication number: WO2022163281A1
Authority: WO; WIPO (PCT)
Prior art keywords: adhesive sheet; pressure; sensitive adhesive; meth; active energy
Prior art date: 2021-01-27

Application number

PCT/JP2021/048543

Other languages

English (en)

French (fr)

Japanese (ja)

Inventor

優那原田

亮太山本

公平広瀬

Original Assignee

三菱ケミカル株式会社

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2021-01-27

Filing date

2021-12-27

Publication date

2022-08-04

2021-12-27 Application filed by 三菱ケミカル株式会社 filed Critical 三菱ケミカル株式会社

2021-12-27 Priority to JP2022578190A priority Critical patent/JPWO2022163281A1/ja

2021-12-27 Priority to CN202180091745.1A priority patent/CN116806245A/zh

2021-12-27 Priority to KR1020237019425A priority patent/KR20230136732A/ko

2022-08-04 Publication of WO2022163281A1 publication Critical patent/WO2022163281A1/ja

Links

239000000853 adhesive Substances 0.000 title claims abstract description 193
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238000004519 manufacturing process Methods 0.000 title claims description 25
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239000000470 constituent Substances 0.000 claims abstract description 33
238000011084 recovery Methods 0.000 claims abstract description 11
238000010030 laminating Methods 0.000 claims abstract description 10
239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 272
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 217
239000000203 mixture Substances 0.000 claims description 57
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238000003475 lamination Methods 0.000 claims description 23
238000005259 measurement Methods 0.000 claims description 21
238000000034 method Methods 0.000 claims description 21
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230000005865 ionizing radiation Effects 0.000 description 1
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
239000004611 light stabiliser Substances 0.000 description 1
235000001510 limonene Nutrition 0.000 description 1
229940087305 limonene Drugs 0.000 description 1
239000004973 liquid crystal related substance Substances 0.000 description 1
FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000000691 measurement method Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
239000006078 metal deactivator Substances 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
230000000116 mitigating effect Effects 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
238000000465 moulding Methods 0.000 description 1
PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
MDYPDLBFDATSCF-UHFFFAOYSA-N nonyl prop-2-enoate Chemical compound CCCCCCCCCOC(=O)C=C MDYPDLBFDATSCF-UHFFFAOYSA-N 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
230000036211 photosensitivity Effects 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920006289 polycarbonate film Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000004080 punching Methods 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000010008 shearing Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
230000001629 suppression Effects 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical class CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
238000001029 thermal curing Methods 0.000 description 1
239000010409 thin film Substances 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
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
239000006097 ultraviolet radiation absorber Substances 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
238000004383 yellowing Methods 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- 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
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- 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
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/29—Laminated material
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- 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
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/20—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive itself
- C09J2301/208—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive itself the adhesive layer being constituted by at least two or more adjacent or superposed adhesive layers, e.g. multilayer adhesive
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/304—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being heat-activatable, i.e. not tacky at temperatures inferior to 30°C
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation

Definitions

the present invention relates to an adhesive sheet that can be suitably used for an image display device having a curved surface, a bendable flexible image display device, and the like.
a pressure-sensitive adhesive sheet that can be suitably used for bonding members for constituting an image display device having a stepped portion on the bonding surface, a pressure-sensitive adhesive sheet with a release film using the pressure-sensitive adhesive sheet, a laminate, and a laminate Laminate sheet, laminate for image display device, flexible image display device, adhesive sheet for flexible display, and method for producing laminate for image display device.
Such a display device has a laminated structure in which multiple sheet members such as a cover lens, a circularly polarizing plate, a touch film sensor, and a light-emitting element are bonded together with a transparent adhesive sheet. When applied, it can be regarded as a laminate in which the member and the adhesive sheet are laminated.
Patent Document 1 by setting the product value of the creep compliance fluctuation value and the relaxation elastic modulus fluctuation value to a suitable range, it is applied to a repeatedly bending device, and the bending state can be maintained for a long period of time.
the pressure-sensitive adhesive for repeatedly bending devices and the pressure-sensitive adhesive that exhibits high resilience such as suppressing deformation of the pressure-sensitive adhesive layer after being released from the bending state in the case of being placed in a curved state and mitigating the effects of being placed in the bending state Sheets and flex laminate members and repeat flex devices are disclosed.
the surface of a member constituting the image display device (also referred to as “image display device constituent member”) is made uneven by wiring, printing, pattern development, surface treatment, or the like.
the pressure-sensitive adhesive sheet for bonding image display device constituent members having such a stepped portion follows the step while being thin, under the limitation that it cannot be thickened due to the demand for thinning of the image display device. If it is not possible to fill all the corners of the adhesive layer, air bubbles may be generated inside the adhesive layer, so the adhesive sheet is required to have high fluidity. However, it has been difficult to stably exhibit resilience and durability in a wide temperature range with a pressure-sensitive adhesive sheet having high fluidity at the time of lamination.
the present invention enables even an image display device component having a stepped portion on the surface to be filled to every corner so as to follow the stepped portion so as not to generate air bubbles, and to display an image.
a laminate having a configuration in which a device component and an adhesive sheet are laminated can exhibit excellent resilience and durability even when bending is performed in a high temperature environment, and when bending is performed in a low temperature environment.
the present invention proposes an active energy ray-curable pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer containing a meth)acrylic polymer (A) and satisfying the following requirements (1) to (3).
(1) It has a thickness of 0.8 mm to 1.5 mm and a strain (creep strain) of 50% or more when a pressure of 1000 Pa is applied at a temperature of 25° C. for 3600 seconds.
(2) After irradiating an active energy ray with a wavelength of 365 nm with an integrated light amount of 2000 to 4000 mJ / cm 2 with a thickness of 0.8 mm to 1.5 mm, a pressure of 1000 Pa at a temperature of 80 ° C. is applied for 180 seconds. creep strain) becomes 10% or more.
the present invention also proposes a release film-attached pressure-sensitive adhesive sheet having a structure in which the active energy ray-curable pressure-sensitive adhesive sheet proposed by the present invention and a release film are laminated.
the present invention also provides a method in which a release film and a member for constituting an image display device having a step with a height difference of 2 ⁇ m or more on the surface to be laminated are laminated via the active energy ray-curable adhesive sheet proposed by the present invention.
a laminate having a structure of
a release film and an image display device constituting member having a step with a height difference of 2 ⁇ m or more on the surface to be laminated are laminated via the active energy ray-curable adhesive sheet proposed by the present invention,
a method for producing a laminate is proposed in which the pressure-sensitive adhesive sheet is irradiated with an active energy ray through the release film from the release film side.
the present invention also proposes a laminated sheet having a structure in which the active energy ray-curable pressure-sensitive adhesive sheet proposed by the present invention and another pressure-sensitive adhesive sheet are laminated.
the present invention also includes a structure in which two image display device constituent members are laminated via the active energy ray-curable pressure-sensitive adhesive sheet proposed by the present invention, and at least one of the image display device constituent members is proposes a layered product for an image display device having a step having a height difference of 2 ⁇ m or more on the contact surface with the pressure-sensitive adhesive sheet.
the present invention also provides a flexible display pressure-sensitive adhesive sheet comprising a pressure-sensitive adhesive layer containing a (meth)acrylic polymer (A),
the thickness is 15 ⁇ m or more and 50 ⁇ m or less,
a member for constituting an image display device having active energy ray curability and having steps with a height difference of 2 to 10 ⁇ m at intervals of 10 mm or less is laminated under the following bonding conditions, there is no foaming around the steps.
a pressure-sensitive adhesive sheet for a flexible display characterized by: (Lamination conditions) a) A pressure-sensitive adhesive sheet having a thickness of 15 to 50 ⁇ m is irradiated with ultraviolet rays so that the integrated amount of light at 365 nm is 2000 to 4000 mJ/cm 2 . b) The pressure-sensitive adhesive sheet is vacuum-bonded to the surface of a substrate having steps with height differences of 2 to 10 ⁇ m at intervals of 10 mm or less under conditions of a press pressure of 0.2 MPa and 30 seconds. c) Perform autoclave treatment under conditions of 70° C., atmospheric pressure of 0.45 MPa, and 20 minutes.
the present invention also provides a method for producing a laminate for image display device comprising two image display device constituent members 1 and 2 laminated via an active energy ray-curable adhesive sheet, comprising:
a method for producing a laminate for an image display device is proposed, which has the following steps 1 to 3, and is characterized by performing steps 1 and 2 and then performing step 3.
Step 1 One surface of the active energy ray-curable pressure-sensitive adhesive sheet proposed by the present invention is attached to the member 1 for constituting an image display device.
Step 2 The active energy ray-curable pressure-sensitive adhesive sheet proposed by the present invention is cured by irradiating it with an active energy ray.
Step 3 The image display device constituting member 2 is adhered to the other surface of the pressure-sensitive adhesive sheet to form a laminate.
the pressure-sensitive adhesive sheet proposed by the present invention fills every corner of the adherend so as to follow the step so as not to generate air bubbles even if there is a step on the sticking surface of the image display device constituent member that is the adherend. can do. Furthermore, the pressure-sensitive adhesive sheet proposed by the present invention exhibits excellent resilience and durability even when a laminate having a configuration in which the pressure-sensitive adhesive sheet and image display device constituent members are laminated is operated to bend in a high-temperature environment. Excellent durability can be exhibited even when a bending operation is performed in a low-temperature environment. Therefore, for example, even when the laminate is folded, curved, or wound up in a high-temperature or low-temperature environment, excellent durability or resilience can be exhibited. From the above points, the pressure-sensitive adhesive sheet proposed by the present invention can be suitably used, for example, as a pressure-sensitive adhesive sheet for flexible displays.
a pressure-sensitive adhesive sheet (referred to as "the present pressure-sensitive adhesive sheet") according to an example of the embodiment of the present invention includes a (meth)acrylic polymer (A), particularly a pressure-sensitive adhesive layer (“the present pressure-sensitive adhesive layer ”) is an active energy ray-curable pressure-sensitive adhesive sheet.
the present pressure-sensitive adhesive layer in the present pressure-sensitive adhesive sheet contains, for example, a (meth)acrylic polymer (A), particularly the (meth)acrylic polymer (A) as a main component resin, preferably a cross-linking agent (B) and/or a polymerization initiator (C) and, if necessary, a pressure-sensitive adhesive composition (referred to as "the present pressure-sensitive adhesive composition”) containing other components.
the "active energy ray-curable adhesive sheet” is a pressure-sensitive adhesive sheet having properties that can be cured by an active energy ray, in other words, an active energy ray-curable adhesive sheet that leaves room for curing by an active energy ray. is the meaning of This pressure-sensitive adhesive sheet may have been cured (also referred to as “temporary curing”) in a state in which there is room for curing by the active energy ray, or may have not been cured at all (referred to as “uncured”). ) and can be cured by active energy rays. If the adhesive sheet is temporarily cured or uncured, the adhesive sheet is cured with active energy rays before or after bonding the adhesive sheet to the adherend ("main curing ), which can result in increased cohesion and improved adhesion.
the "main component resin” means the resin having the highest mass ratio among the resins constituting the pressure-sensitive adhesive layer or the pressure-sensitive adhesive composition.
the content of the main component resin is 70% by mass or more, especially 80% by mass or more, and 90% by mass or more (including 100% by mass) of the resins constituting the present pressure-sensitive adhesive layer or the present pressure-sensitive adhesive composition. may occupy.
the pressure-sensitive adhesive sheet preferably has a thickness of 0.8 mm to 1.5 mm and a strain (creep strain) of 50% or more when a pressure of 1000 Pa is applied at a temperature of 25° C. for 3600 seconds.
the fact that the pressure-sensitive adhesive sheet has a creep strain of 50% or more when a pressure of 1000 Pa is applied at a temperature of 25° C. for 3600 seconds before curing indicates that it is easily deformable in this state. Even if the surface of the member constituting the image display device, which is the adherend, has unevenness, it can be made to follow every corner of the stepped portion, which is preferable.
the pressure-sensitive adhesive sheet preferably has a creep strain of 50% or more, more preferably 100% or more, more preferably 105% or more, particularly 110% or more.
the creep strain is preferably 10000% or less because the shape can be maintained at room temperature or lower.
the creep strain of the present pressure-sensitive adhesive sheet is more preferably 5000% or less, more preferably 2500% or less, further preferably 1000% or less, more preferably 500% or less, particularly 250% or less. % or less is more preferable.
the creep strain in the present pressure-sensitive adhesive sheet is a numerical value when the thickness is 0.8 mm to 1.5 mm. It is necessary to avoid fluctuations in measurement results due to the influence of measurement jigs due to insufficient thickness. To this end, it is necessary to measure the present pressure-sensitive adhesive sheet after adjusting it within a certain range of thickness. By adjusting the thickness of the pressure-sensitive adhesive sheet in advance within the above range and then measuring the creep strain, the creep strain of the pressure-sensitive adhesive sheet can be accurately determined without being affected by the measuring jig.
the above-mentioned "thickness of 0.8 mm to 1.5 mm” means that if the thickness of the adhesive sheet as a measurement sample is less than this range, the thickness of the measurement sample may be adjusted by stacking several sheets. It means to adjust the depth to this range. The same is true when the thickness of the measurement sample is specified in other tests.
the composition and molecular weight of the (meth)acrylic polymer (A) are adjusted, and the type and amount of the cross-linking agent (B) are adjusted. is preferred. However, it is not limited to this means.
the pressure-sensitive adhesive sheet had a thickness of 0.8 mm to 1.5 mm, and was irradiated with an active energy ray having a wavelength of 365 nm in an integrated light amount of 2000 to 4000 mJ/cm 2 , and then a pressure of 1000 Pa was applied at a temperature of 80 ° C. for 180 seconds. It is preferable that the time strain (creep strain) is 10% or more.
This PSA sheet has a strain (creep strain) of 10% or more when a pressure of 1000 Pa is applied at a temperature of 80° C. for 180 seconds after curing.
the creep strain after curing with active energy rays is more preferably 10% or more, more preferably 20% or more, more preferably 30% or more, more preferably 40% or more.
the upper limit of the strain (creep strain) after curing is too high, the pressure-sensitive adhesive sheet may protrude from the end face of the laminate in a high-temperature environment and the end face may become sticky, cohesive peeling may occur during folding, It is preferably 500% or less, more preferably 300% or less, even more preferably 100% or less, and 80% or less because there is a risk of impairing the resilience when opened from the state. is particularly preferred, and 60% or less is most preferred.
the creep strain of the present pressure-sensitive adhesive sheet after curing with active energy rays is also measured after adjusting the thickness of the present pressure-sensitive adhesive sheet to 0.8 mm to 1.5 mm in the same manner as described above. As described above, is based on consideration of the influence of the measuring jig, and is not intended to require the thickness of the pressure-sensitive adhesive sheet to be within the above range.
the composition and molecular weight of the (meth)acrylic polymer (A), which is the base polymer described later, may be adjusted, or the cross-linking agent ( It is preferable to adjust the type and addition amount of B) or to adjust the irradiation dose of the active energy ray.
the type and addition amount of B may be adjusted, or the cross-linking agent ( It is preferable to adjust the type and addition amount of B) or to adjust the irradiation dose of the active energy ray.
This pressure-sensitive adhesive sheet preferably has a recovery rate of 60% or more after 200% deformation at 25° C., which is represented by the following formula when irradiated with an active energy ray having a wavelength of 365 nm with an accumulated amount of light of 2000 to 4000 mJ/cm 2 .
the recovery rate is represented by the following formula.
Restoration rate (%) ⁇ (xy)/x ⁇ x 100 (x is the initial strain applied in the shear direction to the adhesive sheet with a thickness of 0.8 mm to 1.5 mm, and y is the residual strain after 600 seconds after the initial strain was applied for 600 seconds and released. A more specific measurement method is described in Examples.)
the recovery rate of this adhesive sheet after curing is 60% or more, permanent deformation can be suppressed, and the recovery property when unfolded from the folded state is also good. From this point of view, the recovery rate is preferably 70% or more, more preferably 75% or more, and more preferably 80% or more.
the recovery rate of the present pressure-sensitive adhesive sheet is also measured after adjusting the thickness of the pressure-sensitive adhesive sheet to 0.8 mm to 1.5 mm in the same manner as described above. It is intended to take into consideration the influence of the measuring jig, and is not intended to require the thickness of the pressure-sensitive adhesive sheet to be within the above range.
the adhesive sheet Before being cured by active energy rays, the adhesive sheet is preferably in an uncrosslinked state or a slightly crosslinked state, that is, in a state where the gel fraction is 0% or more and 20% or less. From the viewpoint of conformability to irregularities on the adherend surface, the gel fraction is more preferably 10% or less, even more preferably 8% or less, and even more preferably 5% or less.
the gel fraction after curing with active energy rays is 10% or more, the shape stability of the pressure-sensitive adhesive sheet, and the resilience and durability when folded when formed into a laminate can be imparted.
the gel fraction after curing with active energy rays is preferably 10% or more, more preferably 30% or more, and more preferably 40% or more.
the gel fraction after active energy ray curing is preferably 85% or less.
the gel fraction after curing with active energy rays is more preferably 70% or less, more preferably 60% or less, and even more preferably 55% or less.
this pressure-sensitive adhesive sheet is cured by irradiating an active energy ray with a wavelength of 365 nm at an accumulated light amount of 1000 mJ/cm 2 , the gel fraction does not change or increases by less than 0.5% compared to before curing. There may be.
the present pressure-sensitive adhesive sheet may have such a low photosensitivity.
the composition and molecular weight of the (meth)acrylic polymer (A), which is the base polymer, may be adjusted, or the type of the cross-linking agent (B) may be adjusted. It is preferable to adjust the addition amount of the active energy ray, and to adjust the intensity of the active energy ray to be irradiated and the integrated amount of light. However, it is not limited to this means.
the pressure-sensitive adhesive sheet preferably has the following properties (4). (4) Adhesive strength to the surface of soda lime glass at 23° C. 50% RH, peel angle 180°, peel speed 300 mm / min is 1 N / cm or more.
the adhesive strength is 1 N/cm or more, it is preferable because it facilitates positioning and temporary fixation when bonding the image display device constituent members to be described later. From this point of view, the adhesive strength is preferably 1 N/cm or more, more preferably 2 N/cm or more, still more preferably 4 N/cm or more, and particularly preferably 5 N/cm or more. , 10 N/cm or more. Incidentally, the normal upper limit is 40 N/cm.
the pressure-sensitive adhesive sheet also preferably has the following properties (5).
the adhesive strength is 1 N/cm or more, it is preferable because when a laminated body is formed by laminating together with the image display device constituent members described later, delamination or the like does not occur at the time of bending, and durability is improved.
the adhesive strength when irradiated with active energy rays after lamination to soda lime glass is preferably 1 N/cm or more, more preferably 2 N/cm or more, and 3 N/cm or more. It is more preferable that it is 5 N/cm or more. Incidentally, the normal upper limit is 40 N/cm.
the pressure-sensitive adhesive sheet further preferably has the following properties (6).
(6) After irradiating an active energy ray with a wavelength of 365 nm at an integrated light amount of 2000 to 4000 mJ/cm 2 , when the adhesive sheet is laminated to soda lime glass, peeling at 23 ° C. 50% RH and peeling from the surface of the soda lime glass.
Adhesive strength is 1 N/cm or more at an angle of 180° and a peeling speed of 300 mm/min
the adhesive strength is 1 N/cm or more, it is preferable because delamination or the like does not occur at the time of bending when a laminate is formed by laminating together with the image display device constituent members described later, and durability is improved.
the pressure-sensitive adhesive sheet has an adhesive force of 1 N/cm or more, more preferably 2 N/cm or more, more preferably 3 N/cm or more when the adhesive sheet is laminated to soda lime glass after being cured with an active energy ray. /cm or more, and more preferably 5 N/cm or more.
the normal upper limit is 40 N/cm.
the pressure-sensitive adhesive sheet preferably has a thickness of 0.8 mm to 1.5 mm, and a loss tangent obtained by dynamic viscoelasticity measurement in a shear mode at a frequency of 1 Hz is 0.8 or more at -30°C. It is more preferably 1 or more, especially 1.2 or more, still more preferably 1.5 or more, and more preferably 2.0 or less, still more preferably 1.8 or less.
the loss tangent (tan ⁇ ) of the present adhesive sheet is within the above range, even if the adherend has irregularities on the adherend surface, the adhesive resin can flow and fill the stepped portions by heating, which is preferable.
the pressure-sensitive adhesive sheet after curing the active energy ray, that is, after irradiating the active energy ray with a wavelength of 365 nm in an integrated light amount of 2000 to 4000 mJ/cm 2 , the pressure-sensitive adhesive sheet has a thickness of 0.8 mm to 1.5 mm and a shear at a wave number of 1 Hz.
the loss tangent obtained by dynamic viscoelasticity measurement in mode is preferably 0.5 or more and 2.3 or less in the range of -30°C or more and -10°C or less.
the loss tangent (tan ⁇ ) after curing is within the above range, even if the laminate using the present pressure-sensitive adhesive sheet is folded in a low-temperature environment, peeling or buckling at the interface of image display device constituent members, and image display device constituent members do not occur. It is preferable because it does not cause cracks or the like.
the loss tangent (tan ⁇ ) in the range of ⁇ 30° C. or higher and ⁇ 10° C. or lower is preferably 0.5 or higher and 2.3 or lower, especially 0.8 or higher or 2.0 or lower. is more preferable, and among them, 1.1 or more or 1.9 or less is more preferable.
the pressure-sensitive adhesive sheet has a thickness of 0.8 mm to 1.5 mm, and the maximum loss tangent obtained when dynamic viscoelasticity is measured in a shear mode at a frequency of 1 Hz is ⁇ 20° C. or less. is preferred. It is preferable that the maximum point of the loss tangent is ⁇ 20° C. or less, because the laminate can have durability when folded. From this point of view, the maximum point of the loss tangent is more preferably ⁇ 25° C. or less, more preferably ⁇ 30° C. or less, even more preferably ⁇ 33° C. or less, and particularly preferably ⁇ 35° C. or less. Also, the lower limit is usually -60° C. or higher.
the loss tangent before or after curing of the pressure-sensitive adhesive sheet is also measured after adjusting the thickness of the pressure-sensitive adhesive sheet to 0.8 mm to 1.5 mm in the same manner as described above. As described above, is based on consideration of the influence of the measuring jig, and is not intended to require the thickness of the pressure-sensitive adhesive sheet to be within the above range.
the composition and molecular weight of the (meth)acrylic polymer (A), which is the base polymer described later, may be adjusted, or the cross-linking agent (B ) is preferably adjusted and the amount of active energy ray irradiation is adjusted.
the cross-linking agent (B ) is preferably adjusted and the amount of active energy ray irradiation is adjusted.
the adhesive sheet has a thickness of 0.8 mm to 1.5 mm and a storage modulus (G′) of 0.01 to 0.2 MPa obtained by dynamic viscoelasticity measurement in a shear mode at a temperature of 25° C. and a frequency of 1 Hz. It is preferable to have When the storage elastic modulus (G′) of the present pressure-sensitive adhesive sheet is within such a range, even if the adherend surface of the adherend has unevenness, it can be attached so as to follow the unevenness and absorb the unevenness.
the storage elastic modulus (G') of the present pressure-sensitive adhesive sheet is preferably 0.01 MPa or more and 0.2 MPa or less at a temperature of 25° C. and a frequency of 1 Hz, especially 0.02 MPa or more or 0.1 MPa or less. and more preferably 0.03 MPa or more or 0.09 MPa or less.
the pressure-sensitive adhesive sheet after curing the active energy ray, that is, after irradiating the active energy ray with a wavelength of 365 nm in an integrated light amount of 2000 to 4000 mJ/cm 2 , the pressure-sensitive adhesive sheet has a thickness of 0.8 mm to 1.5 mm and a temperature of 25°C.
the storage elastic modulus (G') obtained by dynamic viscoelasticity measurement in shear mode at a frequency of 1 Hz is preferably 0.02 MPa or more and 0.24 MPa or less.
the storage elastic modulus (G′) after curing of the pressure-sensitive adhesive sheet is within such a range, when a layered product is formed by laminating it with an image display device item painter member described later, delamination or the like does not occur when bending, and the adhesive sheet is durable. good properties.
the storage elastic modulus (G′) after curing of the pressure-sensitive adhesive sheet is preferably 0.02 MPa or more and 0.24 MPa or less at a temperature of 25° C. and a frequency of 1 Hz. It is preferably 0.20 MPa or less, more preferably 0.04 MPa or more or 0.10 MPa or less.
the storage elastic modulus (G') of the pressure-sensitive adhesive sheet before or after curing is also measured after adjusting the thickness of the pressure-sensitive adhesive sheet to 0.8 mm to 1.5 mm in the same manner as described above.
the reason for this is that the influence of the measuring jig is considered, and the thickness of the pressure-sensitive adhesive sheet is not necessarily within the above range.
the composition and molecular weight of the (meth)acrylic polymer (A), which is the base polymer described later, may be adjusted, or the cross-linking agent may be adjusted. It is preferable to adjust the type and amount of addition of (B), and to adjust the dose of active energy rays. However, it is not limited to this means.
the pressure-sensitive adhesive composition is a composition containing a (meth)acrylic polymer (A), preferably a cross-linking agent (B) and/or a polymerization initiator (C), and optionally other components. .
the pressure-sensitive adhesive composition contains a (meth)acrylic polymer (A), especially as a main component resin. That is, the (meth)acrylic polymer (A) is a resin having the highest mass ratio among the resins constituting the pressure-sensitive adhesive composition. At this time, among the resins constituting the present pressure-sensitive adhesive composition, the mass ratio of the (meth)acrylic polymer (A) is 50% by mass or more, especially 70% by mass or more, especially 80% by mass or more, especially 90% by mass. % or more (including 100% by mass).
the (meth)acrylic polymer (A) As the (meth)acrylic polymer (A), the following formula 1 (wherein R 1 represents a hydrogen atom or a methyl group and R 2 represents a linear or branched alkyl having 4 to 18 carbon atoms group or an alicyclic hydrocarbon), and is preferably obtained by polymerizing a polymer component containing 50% by mass or more of the monomer component.
the (meth)acrylic polymer (A) is more preferably polymerized to contain 55% by mass or more of the monomer component as a polymerization component, and particularly preferably polymerized to contain 60% by mass or more.
(meth)acrylic means acrylic and methacrylic
(meth)acryloyl means acryloyl and methacryloyl
(meth)acrylate means acrylate and methacrylate, respectively.
(co)polymer is meant to include polymers and copolymers.
Examples of the monomer represented by Formula 1 include n-butyl (meth)acrylate, isobutyl (meth)acrylate, sec-butyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, isopentyl ( meth) acrylate, neopentyl (meth) acrylate, hexyl (meth) acrylate, cyclohexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth)acrylate, isononyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, unde
butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate and lauryl (meth)acrylate is particularly preferable.
the (meth)acrylic polymer (A) is preferably a copolymer having "another copolymerizable monomer" other than the monomer component as a copolymerization component.
the above-mentioned "other copolymerizable monomer” is preferably contained in the (meth)acrylic polymer (A) in an amount of 1 to 30% by mass, and is contained in a proportion of 2% by mass or more or 25% by mass or less. is more preferred.
Examples of the “other copolymerizable monomer” include (a) a carboxyl group-containing monomer (hereinafter also referred to as “copolymerizable monomer a1”), (b) a hydroxyl group-containing monomer (hereinafter also referred to as “copolymerizable monomer a2").
Examples of the copolymerizable monomer a1 include (meth)acrylic acid, carboxyethyl (meth)acrylate, carboxypropyl (meth)acrylate, carboxybutyl (meth)acrylate, ⁇ -carboxypolycaprolactone mono(meth)acrylate, 2- (Meth) acryloyloxyethyl hexahydrophthalate, 2-(meth) acryloyloxypropyl hexahydrophthalate, 2-(meth) acryloyloxyethyl phthalate, 2-(meth) acryloyloxypropyl phthalate, 2-(meth) ) ) acryloyloxyethyl maleate, 2-(meth)acryloyloxypropyl maleate, 2-(meth)acryloyloxyethyl succinate, 2-(meth)acryloyloxypropyl succinate, crotonic acid, fumaric acid, maleic acid, itacon Men
Examples of the copolymerizable monomer a2 include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxy-1-methylethyl acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxy Butyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, glycerin mono (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, polyethylene glycol polypropylene glycol mono (meth) acrylate, polyethylene glycol Hydroxyalkyl (meth)acrylates such as polybutylene glycol mono(meth)acrylate, polypropylene glycol polybutylene glycol mono(meth)acrylate and hydroxyphenyl(meth)acrylate can be mentioned. These may be used alone or in combination of two or more.
Examples of the copolymerizable monomer a3 include aminoalkyl (meth)acrylates such as aminomethyl (meth)acrylate, aminoethyl (meth)acrylate, aminopropyl (meth)acrylate, aminoisopropyl (meth)acrylate, N-alkylamino Examples include N,N-dialkylaminoalkyl (meth)acrylates such as alkyl (meth)acrylates, N,N-dimethylaminoethyl (meth)acrylate, and N,N-dimethylaminopropyl (meth)acrylate. These may be used alone or in combination of two or more.
Examples of the copolymerizable monomer a4 include glycidyl (meth)acrylate, methylglycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate glycidyl ether. . These may be used alone or in combination of two or more.
Examples of the copolymerizable monomer a5 include (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N-butyl(meth)acrylamide, N-methylol(meth)acrylamide, N-methylolpropane(meth)acrylamide, Mention may be made of N-methoxymethyl(meth)acrylamide, N-butoxymethyl(meth)acrylamide, diacetone(meth)acrylamide, maleic acid amide and maleimide. These may be used alone or in combination of two or more.
Examples of the copolymerizable monomer a6 include compounds having a vinyl group in the molecule.
Examples of such compounds include functional monomers having functional groups such as alkoxylalkyl groups such as ethoxydiethylene glycol acrylate, methoxytriethylene glycol acrylate, methoxypolyethylene glycol acrylate, methoxydipropylene glycol acrylate, and methoxypolypropylene glycol acrylate.
polyalkylene glycol di(meth)acrylates and vinyl ester monomers such as vinyl acetate, N-vinyl-2-pyrrolidone, vinyl propionate and vinyl laurate, and styrene, chlorostyrene, chloromethylstyrene, ⁇ -methylstyrene and Other aromatic vinyl monomers such as substituted styrene can be exemplified. These may be used alone or in combination of two or more.
Examples of the copolymerizable monomer a7 include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, i-propyl (meth)acrylate, and the like. These may be used alone or in combination of two or more.
the macromonomer as the copolymerizable monomer a8 is a macromonomer having a terminal functional group and a high-molecular-weight skeleton component.
the "other copolymerizable monomer” is the copolymerizable monomer a8
the (meth)acrylic polymer (A) is a copolymer containing a macromonomer-derived structural unit.
the skeleton component of the macromonomer is preferably composed of an acrylic acid ester polymer or a vinyl polymer.
the (meth)acrylate having a linear or branched alkyl group having 4 to 18 carbon atoms, the copolymerizable monomer a1, the copolymerizable monomer a2, the copolymerizable monomer a6, the copolymerizable Those exemplified by the monomer a7 and the like can be mentioned, and these can be used alone or in combination of two or more.
the number average molecular weight of the macromonomer is preferably 1,000 or more, more preferably 1,500 or more, and even more preferably 2,000 or more. The upper limit of the number average molecular weight is usually 20,000.
the macromonomer is a macromonomer obtained by copolymerizing a (meth)acrylate having a linear or branched alkyl group having 1 to 3 carbon atoms. It is good because it can improve the properties.
the number average molecular weight of such a macromonomer is preferably 1,000 to 10,000, particularly preferably 1,500 or more or 5,000 or less, and still more preferably 2,000 or more or 4,000 or less.
the macromonomer is a macromonomer obtained by copolymerizing a (meth)acrylate having a linear or branched alkyl group having 8 to 18 carbon atoms, the adhesion surface of the adherend becomes more uneven.
the number average molecular weight of such a macromonomer is preferably 2,000 to 20,000, particularly preferably 3,000 or more or 15,000 or less, and still more preferably 4,000 or more or 10,000 or less.
a macromonomer can be introduced as a branch component of the graft copolymer, and the (meth)acrylic acid ester copolymer can be made into a graft copolymer.
a (meth)acrylic polymer (A) comprising a copolymer containing a macromonomer-derived structural unit as a branch component can be used. Therefore, the properties of the main chain and the side chains of the graft copolymer can be changed by selecting the copolymerizable monomer a8 and the other monomers and blending ratio.
the copolymerization ratio of the macromonomer in the (meth)acrylic polymer (A) is preferably 30% by mass or less in terms of imparting fluidity during hot-melt, more preferably 2 % by mass or more and 15% by mass or less, more preferably 3% by mass or more and 10% by mass or less, particularly preferably 4% by mass or more and 7% by mass or less.
Examples of the copolymerizable monomer a9 include benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, nonylphenol EO-modified (meth)acrylate, and the like. These may be used alone or in combination of two or more.
Examples of the copolymerizable monomer a10 include (meth)acryl-modified silicone, 2-acryloyloxyethyl acid phosphate, 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-- Tetrafluoropropyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 1H,1H,5H-octafluoropentyl (meth)acrylate, 1H,1H,2H,2H-tridecafluoro- Examples include fluorine-containing monomers such as n-octyl (meth)acrylate. These may be used alone or in combination of two or more.
the glass transition temperature of at least one of the (meth)acrylic acid ester-derived repeating units of the acrylic polymer (A) is preferably -70 to 0°C.
the glass transition temperature of the copolymer component means a value calculated by the Fox formula from the glass transition temperature of the polymer obtained from the homopolymer of each component of the copolymer and the composition ratio.
the glass transition temperature of at least one of the (meth)acrylic acid ester-derived repeating units of the acrylic polymer (A) is -70. ⁇ 0°C is preferred.
(Meth)acrylic acid esters constituting such repeating units include, for example, n-butyl acrylate, n-hexyl acrylate, n-octyl acrylate, n-nonyl acrylate, n-decyl acrylate, 2-ethylhexyl acrylate, 2 -ethylhexyl methacrylate, 2-methylhexyl acrylate, isooctyl acrylate, isononyl acrylate, isodecyl acrylate, isodecyl methacrylate, isostearyl acrylate, isostearyl (meth)acrylate, multi-branched stearyl acrylate, multi-branched stearyl (meth)acrylate, etc. can be mentioned, but are not limited to these.
the glass transition temperature of at least one repeating unit derived from the (meth)acrylic acid ester of the acrylic polymer (A) is 20 to 120° C.
excellent workability and storage are obtained. It is preferable because stability can be maintained.
the glass transition temperature (Tg) is preferably 30° C. to 120° C., especially 40° C. or higher or 110° C. or lower, especially 50° C. or higher, because it affects the hot-melt temperature of the pressure-sensitive adhesive sheet. Alternatively, it is more preferably 100° C. or less. If there is a repeating unit having such a glass transition temperature (Tg), it is possible to maintain excellent workability and storage stability by adjusting the molecular weight, and to adjust it so that it hot melts at 50 ° C. or higher. can.
(Meth)acrylic acid esters constituting such repeating units include, for example, methyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, n-butyl methacrylate, t-butyl acrylates, isobutyl acrylate, isobutyl methacrylate, isobornyl acrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 1,4-cyclohexanedimethanol monoacrylate, tetrahydrofurfuryl methacrylate, benzyl acrylate, benzyl methacrylate, phenoxyethyl acrylate, phenoxyethyl methacrylate, etc. can be mentioned.
the (meth)acrylic polymer (A) is preferably a block copolymer and/or a graft copolymer from the viewpoint of imparting hot-melt properties to the pressure-sensitive adhesive.
a block copolymer or a graft copolymer as the (meth)acrylic polymer (A), a pressure-sensitive adhesive sheet having excellent shape stability and hot-melt properties can be obtained.
the block copolymer refers to a copolymer having a plurality of polymer chains containing repeating units derived from (meth)acrylic acid ester, and having a plurality of polymer chains with different chemical structures bonded in a straight chain.
some blocks of the block copolymer contain repeating units derived from the macromonomer.
graft copolymers are copolymers containing repeating units derived from (meth)acrylic acid ester as a trunk component, and depending on the method of introducing the branch component, they can be comb-shaped polymers, brush-shaped polymers, star polymers, palm-shaped polymers, and so on.
a copolymer containing repeating units derived from a macromonomer as a branch component of the graft copolymer is preferred.
a graft copolymer containing repeating units derived from a macromonomer is used as the base polymer.
block copolymers containing repeating units derived from macromonomers it is common to graft copolymers that the repeating units derived from macromonomers aggregate and phase-separate to exert an effect. It can be expected that a block copolymer containing a can also obtain the same effect as a graft copolymer containing a macromonomer.
the (meth)acrylic polymer (A) is a copolymer containing a structural unit derived from a macromonomer as described above, if the copolymerization ratio of the macromonomer is 2% by mass or more, the hot-melt property On the other hand, if it is 30% by mass or less, when it is laminated with the image display device constituent members described later to form a laminate, delamination or the like does not occur during bending, and durability is improved.
the copolymerization ratio of the macromonomer in the (meth)acrylic polymer (A) is preferably 2% by mass or more, more preferably 3% by mass or more, and more preferably 4% by mass or more. On the other hand, it is preferably 30% by mass or less, more preferably 15% by mass or less, more preferably 10% by mass or less, more preferably 8% by mass or less, even more preferably 7% by mass or less.
a (meth)acrylic polymer (A) using a macromonomer obtained by copolymerizing a (meth)acrylate having a linear or branched alkyl group having 1 to 3 carbon atoms is used as the macromonomer.
the glass transition temperature of the repeating unit derived from the macromonomer is preferably 20 to 150°C, more preferably 40°C or higher or 130°C or lower, and more preferably 60°C or higher or 120°C or lower.
the content of the copolymer component having a glass transition temperature within the above range is preferably 3% by mass or more, more preferably 4% by mass or more, relative to the (meth)acrylic polymer (A).
it is preferably 10% by mass or less, more preferably 9% by mass or less, more preferably 8% by mass or less, even more preferably 7% by mass or less.
the repeating unit derived from the macromonomer that is, the copolymer component having a glass transition temperature of 20 to 150 ° C.
the cross-linking agent (B) is a compound or composition that forms a cross-linked structure in the pressure-sensitive adhesive composition, and is a compound having two or more cross-linkable functional groups.
the present pressure-sensitive adhesive composition contains the cross-linking agent (B)
the present pressure-sensitive adhesive composition forms a cross-linked structure and can impart durability and restorability to the present pressure-sensitive adhesive sheet.
crosslinkable functional groups examples include isocyanate groups, epoxy groups, (meth)acryloyl groups, thioisocyanate groups, primary or secondary amino groups, and thiol groups. These may be protected with a suitable protecting group.
crosslinkable functional groups contained in the crosslinker include only epoxy groups, only isocyanate groups, only (meth)acryloyl groups, only thioisocyanate groups, only thiol groups, only primary or secondary amino groups, epoxy and (meth)acryloyl groups, and combinations of isocyanate groups and (meth)acryloyl groups.
a polyfunctional (meth)acrylate (b) having two or more (meth)acryloyl groups is used as the cross-linking agent (B). is preferred.
the content of the polyfunctional (meth)acrylate (b) is preferably 0.5 parts by mass or more, preferably 1 part by mass or more, with respect to 100 parts by mass of the (meth)acrylic polymer (A). Among them, 1.5 parts by mass or more is more preferable. Regarding the upper limit, it is preferably 10 parts by mass or less, more preferably 7 parts by mass or less, from the viewpoint of maintaining appropriate flexibility and ensuring followability to the adherend when bent. It is more preferably 5 parts by mass or less, more preferably 3 parts by mass or less, particularly preferably 2 parts by mass or less.
the amount is preferably 5 parts by mass or less, especially from the viewpoint of imparting flexibility to the extent that it can follow the step. 3 parts by mass or less, more preferably 2 parts by mass or less.
Polyfunctional (meth)acrylates (b) include, for example, 1,4-butanediol di(meth)acrylate, glycerin di(meth)acrylate, neopentyl glycol di(meth)acrylate, glycerin glycidyl ether di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, tricyclodecane dimethacrylate, tricyclodecanedimethanol di(meth)acrylate, bisphenol A polyethoxydi(meth)acrylate, bisphenol A polypropoxy di (meth) acrylate, bisphenol F polyethoxy di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, trimethylolpropane trioxyethyl (meth) acrylate, ⁇ -
the adhesive composition may further contain a monofunctional (meth)acrylate component (D) having one (meth)acryloyl group.
a monofunctional (meth)acrylate component By including a monofunctional (meth)acrylate component, the molecular weight between cross-linking points of the cured product can be increased, so that the degree of freedom of movement of the molecular chains is increased, and the components constituting the image display device are bonded via the pressure-sensitive adhesive sheet.
the pressure-sensitive adhesive sheet made of the pressure-sensitive adhesive composition can be deformed accordingly.
Examples of the monofunctional (meth)acrylate component (D) include ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, Acrylate, amyl (meth)acrylate, isoamyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, octyl (meth)acrylate, isooctyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate Acrylate, dodecyl (meth)acrylate, isododecyl (meth)acrylate, tetradecyl (meth)acrylate, stearyl (meth)acrylate, isostearyl (meth)acrylate
the content ratio by mass of the polyfunctional (meth)acrylate (b) and the monofunctional (meth)acrylate component (D) is the polyfunctional (meth)acrylate (b):
Monofunctional (meth)acrylate (D) is preferably 1:0.1 to 1:9, more preferably 1:1 to 1:9, and preferably 1:2 to 1:9. More preferred. Within this range, the amount of the monofunctional (meth)acrylate component is not too large, and there is no concern that the sensitivity to light will decrease and the productivity will decrease.
the polymerization initiator (C) imparts active energy ray curability to the present pressure-sensitive adhesive sheet, and may be any compound that generates radicals by means of active energy rays.
the polymerization initiator (C) is roughly classified into two groups according to the mechanism of radical generation: a cleavage-type photoinitiator capable of cleaving and decomposing a single bond of the polymerization initiator itself to generate radicals, and an excited initiator. and a hydrogen abstraction type photoinitiator capable of forming an exciplex with a hydrogen donor in the system and transferring hydrogen of the hydrogen donor.
the polymerization initiator (C) may be either a cleavage photoinitiator or a hydrogen abstraction photoinitiator, each of which may be used alone or a mixture of both may be used. may be used alone or in combination of two or more.
a hydrogen abstraction type photoinitiator is used as the photoinitiator, a hydrogen abstraction reaction also occurs from the acrylic (co)polymer, and not only the active energy ray-curable compound but also the acrylic (co)polymer has a crosslinked structure. It is preferable in terms of being able to form a crosslinked structure with many crosslinked points.
cleavage type photoinitiator when used as the polymerization initiator (C), once radicals are generated, it decomposes and deactivates, which is preferable in that there is no risk of unexpected reaction or deterioration after curing.
cleavage-type photoinitiators examples include 2,2-dimethoxy-1,2-diphenylethan-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one. , 1-(4-(2-hydroxyethoxy)phenyl)-2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1-[4- ⁇ 4-(2-hydroxy-2- Methyl-propionyl)benzyl ⁇ phenyl]-2-methyl-propan-1-one, oligo(2-hydroxy-2-methyl-1-(4-(1-methylvinyl)phenyl)propanone), phenylglyoxylic acid methyl, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one , 2-(dimethylamino)-2-[(4-methylpheny
Hydrogen abstraction photoinitiators include, for example, benzophenone, 4-methyl-benzophenone, 2,4,6-trimethylbenzophenone, 4-phenylbenzophenone, 3,3'-dimethyl-4-methoxybenzophenone, 4-(meth)acryloyl Oxybenzophenone, methyl 2-benzoylbenzoate, methyl benzoylformate, bis(2-phenyl-2-oxoacetic acid)oxybisethylene, 4-(1,3-acryloyl-1,4,7,10,13-pentaoxo tridecyl)benzophenone, thioxanthone, 2-chlorothioxanthone, 3-methylthioxanthone, 2,4-dimethylthioxanthone, 2-methylanthraquinone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, 2-aminoanthraquinone and derivatives thereof, etc. can be mentioned.
the content of the polymerization initiator (C) is not particularly limited.
“Other components" other than the above contained in the present pressure-sensitive adhesive composition include, for example, silane coupling agents, tackifying resins, plasticizers, antioxidants, light stabilizers, metal deactivators, if necessary.
Various additives such as a curing agent, anti-aging agent, hygroscopic agent, polymerization inhibitor, ultraviolet absorber, anticorrosive agent, inorganic particles, sensitizer and pigment can be incorporated as appropriate.
the amounts of these additives are typically preferably selected so as not to adversely affect the curing of the adhesive sheet or adversely affect the physical properties of the adhesive sheet.
a reaction catalyst such as a tertiary amine compound, a quaternary ammonium compound, a tin laurate compound, or the like may be appropriately contained.
silane coupling agent examples include compounds having a hydrolyzable functional group such as an alkoxy group together with an unsaturated group such as a vinyl group, an acryloxy group and a methacryloxy group, an amino group, an epoxy group, and the like. .
silane coupling agents include N-( ⁇ -aminoethyl)- ⁇ -aminopropyltrimethoxysilane, N-( ⁇ -aminoethyl)- ⁇ -aminopropylmethyldimethoxysilane, ⁇ -aminopropyl Examples include triethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -methacryloxypropyltrimethoxysilane, and the like. Among them, ⁇ -glycidoxypropyltrimethoxysilane or ⁇ -methacryloxypropyltrimethoxysilane can be preferably used from the viewpoint of good adhesiveness and little discoloration such as yellowing.
the silane coupling agents may be used singly or in combination of two or more.
silane coupling agent When the silane coupling agent is contained, it is preferably 0.1 to 5 parts by mass with respect to 100 parts by mass of the (meth)acrylic polymer, and is preferably 0.2 parts by mass or more or 3 parts by mass or less. More preferred. Coupling agents such as organic titanate compounds can also be effectively used in the same manner as silane coupling agents.
the present pressure-sensitive adhesive composition can contain a hydrocarbon tackifier in order to impart stickiness and hot-melt properties to the present pressure-sensitive adhesive sheet.
Hydrocarbon tackifiers include terpene resins such as polyterpenes (e.g., ⁇ -pinene-based resins, ⁇ -pinene-based resins, and limonene-based resins) and aromatic-modified polyterpene resins (e.g., phenol-modified polyterpene resins), and coumaran-indene.
Resins C5-based hydrocarbon resins, C9-based hydrocarbon resins, C5/C9-based hydrocarbon resins, petroleum-based resins such as dicyclopentadiene-based resins, modified rosins, hydrogenated rosins, polymerized rosins, rosins such as rosin esters can be mentioned.
the hydrocarbon tackifier is preferably compatible with the present pressure sensitive adhesive composition.
the content of the hydrocarbon tackifier is not particularly limited. It is preferably 0.1 to 20 parts by mass, more preferably 0.5 parts by mass or more or 15 parts by mass or less, based on 100 parts by mass of the (meth)acrylic polymer.
silane coupling agents and tackifiers By including these silane coupling agents and tackifiers, it is possible to suitably prepare a pressure-sensitive adhesive composition having excellent adhesive properties.
this adhesive sheet in addition to the (meth)acrylic polymer (A), if necessary, a crosslinking agent (B) and / or a polymerization initiator (C), and optionally other components are mixed in predetermined amounts to prepare the present pressure-sensitive adhesive composition, the pressure-sensitive adhesive composition is formed into a sheet, and if necessary, the curable compound is crosslinked or polymerized to be cured, and the present pressure-sensitive adhesive sheet should be made.
a crosslinking agent (B) and / or a polymerization initiator (C) e.g., it is not limited to this method.
the raw materials are kneaded using a temperature-controllable kneader (e.g., single-screw extruder, twin-screw extruder, planetary mixer, twin-screw mixer, pressure kneader, etc.). Just do it.
a temperature-controllable kneader e.g., single-screw extruder, twin-screw extruder, planetary mixer, twin-screw mixer, pressure kneader, etc.
various additives such as silane coupling agents and antioxidants may be blended in advance with the resin and then supplied to the kneader, or all the materials may be melted and mixed in advance.
a masterbatch in which only the additive is concentrated in the resin in advance may be prepared and supplied.
Methods for forming the present pressure-sensitive adhesive composition into a sheet include known methods such as wet lamination, dry lamination, extrusion casting using a T-die, extrusion lamination, calendering, inflation, injection molding, and injection molding.
a liquid curing method or the like can be employed.
the wet lamination method, the extrusion casting method, and the extrusion lamination method are suitable for producing a sheet.
the present pressure-sensitive adhesive composition contains a radical initiator
a cured product can be produced by curing by irradiating heat and/or active energy rays.
the present pressure-sensitive adhesive sheet can be produced by irradiating heat and/or active energy rays to a molded article, for example, a sheet formed from the present pressure-sensitive adhesive composition.
the active energy rays to be irradiated include ⁇ rays, ⁇ rays, ⁇ rays, ionizing radiation such as neutron rays and electron beams, ultraviolet rays, visible rays, and the like. Ultraviolet rays are preferable from the viewpoint of suppression and reaction control.
the irradiation energy, irradiation time, irradiation method, and the like of the active energy ray are not particularly limited as long as the initiator can be activated to polymerize the (meth)acrylate component.
the present pressure-sensitive adhesive composition can be dissolved in an appropriate solvent and various coating techniques can be used.
the pressure-sensitive adhesive sheet can also be obtained by thermal curing in addition to the active energy ray irradiation curing described above.
the thickness of the adhesive sheet can be adjusted by the coating thickness and the solid content concentration of the coating liquid.
the present pressure-sensitive adhesive sheet may have a single-layer structure composed of the present pressure-sensitive adhesive layer, or may have a multi-layer structure of two or more layers provided with the present pressure-sensitive adhesive layer.
the composition of the layers other than the layer composed of the pressure-sensitive adhesive composition is arbitrary.
the pressure-sensitive adhesive composition forming a layer other than the present pressure-sensitive adhesive layer also It is preferably formed from a pressure-sensitive adhesive composition containing a (meth)acrylic polymer, and more preferably contains the same (meth)acrylic polymer (A) as that of the present pressure-sensitive adhesive layer. Furthermore, it is more preferable that layers other than the pressure-sensitive adhesive layer also contain a cross-linking agent (B) and/or a polymerization initiator (C).
B cross-linking agent
C polymerization initiator
the pressure-sensitive adhesive sheet has a multi-layer structure of two or more layers, it is preferable that at least the outermost layer, the backmost layer, or both layers correspond to the pressure-sensitive adhesive layer. All the layers may be layers corresponding to the pressure-sensitive adhesive layer.
the thickness of the layer corresponding to the pressure-sensitive adhesive layer preferably accounts for 10% or more and 100% or less of the total thickness of the pressure-sensitive adhesive sheet. % or more or 70% or less, more preferably 20% or more or 50% or less.
the thickness of the pressure-sensitive adhesive sheet Since the bending stress at the time of bending or bending is proportional to the thickness, if the thickness of the pressure-sensitive adhesive sheet is 50 ⁇ m or less, the stress at the time of bending or bending can be alleviated, and the thickness of the laminate can be reduced. In addition, it can contribute to thinning of the flexible image display device. On the other hand, when the thickness is 15 ⁇ m or more, the handling property is good, and even if there is an uneven portion having a height difference of 2 ⁇ m or more and 10 ⁇ m or less in the constituent member of the image display device, it is possible to follow the step.
the thickness of the pressure-sensitive adhesive sheet is preferably 50 ⁇ m or less, more preferably 45 ⁇ m or less, more preferably 40 ⁇ m or less, particularly 35 ⁇ m or less.
the lower limit is preferably 15 ⁇ m or more, more preferably 17 ⁇ m or more, and more preferably 20 ⁇ m or more.
the pressure-sensitive adhesive sheet is thin as described above, it can be deformed to follow the unevenness on the surface of the member for an image display device and penetrate into the unevenness. Therefore, the surface of the pressure-sensitive adhesive sheet, that is, the surface opposite to the adhesive surface can be made smooth by absorbing the unevenness. At this time, if the height difference of the unevenness is 12% or less of the thickness of the present pressure-sensitive adhesive sheet, it can be absorbed.
An example of the present pressure-sensitive adhesive sheet is a pressure-sensitive adhesive sheet for a flexible display, which has a pressure-sensitive adhesive layer containing a (meth)acrylic polymer (A), has a thickness of 15 ⁇ m or more and 50 ⁇ m or less, and exhibits active energy ray curability. and having a difference in height of 2 ⁇ m or more, for example, steps of 2 to 10 ⁇ m at intervals of 10 mm or less.
a pressure-sensitive adhesive sheet for a flexible display can be mentioned. (Lamination conditions) a) A pressure-sensitive adhesive sheet having a thickness of 15 to 50 ⁇ m is irradiated with ultraviolet rays so that the integrated amount of light at 365 nm is 2000 to 4000 mJ/cm 2 .
the pressure-sensitive adhesive sheet is vacuum-bonded to the surface of a base material having a difference in height of 2 ⁇ m or more, for example, 2 to 10 ⁇ m at intervals of 10 mm or less under the conditions of a press pressure of 0.2 MPa and 30 seconds.
This pressure-sensitive adhesive sheet can also be used as a single pressure-sensitive adhesive sheet.
the present pressure-sensitive adhesive composition may be directly applied to a member for an image display device to be described later to form a sheet, or the pressure-sensitive adhesive composition may be directly extruded or injected into a mold to obtain the present pressure-sensitive adhesive sheet. can be used.
the present pressure-sensitive adhesive sheet can also be used by directly filling the present pressure-sensitive adhesive composition between image display device constituent members.
this pressure-sensitive adhesive sheet can be used by being laminated with other pressure-sensitive adhesive sheets.
other pressure-sensitive adhesive sheets are more suitable for the flexible image display device if they are more flexible than the present pressure-sensitive adhesive sheet.
Such other adhesive sheets have a gel fraction of 70% or more, a thickness of 0.8 mm to 1.5 mm, and a maximum loss tangent obtained by dynamic viscoelasticity measurement in a shear mode at a frequency of 1 Hz.
a pressure-sensitive adhesive sheet having a temperature of -25°C or less can be mentioned.
the maximum point of the loss tangent is ⁇ 25° C. or less, it is preferable because it can be restored even when it is bent at high and low temperatures.
the maximum point of the loss tangent of the other PSA sheet is preferably ⁇ 25° C. or lower, more preferably ⁇ 30° C. or lower, and more preferably ⁇ 35° C. or lower.
the pressure-sensitive adhesive sheet can be used as a pressure-sensitive adhesive sheet with a release film (referred to as a "pressure-sensitive adhesive sheet with a release film") comprising the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition and a release film.
a pressure-sensitive adhesive sheet with a release film comprising the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition and a release film.
the present pressure-sensitive adhesive composition can be in the form of a release film-attached pressure-sensitive adhesive sheet formed by molding a single-layer or multilayer sheet on a release film.
polyester film examples include polyester film, polyolefin film, polycarbonate film, polystyrene film, acrylic film, triacetylcellulose film, and fluororesin film.
polyester films and polyolefin films are particularly preferred.
the thickness of the release film is not particularly limited. Among them, for example, from the viewpoint of workability and handleability, the thickness is preferably 25 ⁇ m to 500 ⁇ m, more preferably 38 ⁇ m or more or 250 ⁇ m or less, and more preferably 50 ⁇ m or more or 200 ⁇ m or less.
the release film is preferably a polyester-based film, and from the standpoint of releasability, it is preferable that the release film be easily peeled off even after irradiation with active energy rays. From this point of view, when the active energy ray with a wavelength of 365 nm is irradiated with an accumulated light amount of 2000 to 4000 mJ/cm 2 , the peel force for the present adhesive sheet is 0.1 N/cm or less at a peel angle of 180° and a peel speed of 300 mm/min. It is preferable to be
a laminate (referred to as "this laminate") according to an example of an embodiment of the present invention includes a release film and a member for constituting an image display device having a step with a height difference of 2 ⁇ m or more on the surface to be laminated, It is a layered product having a configuration in which layers are layered via an adhesive sheet.
the release film of the laminate is the same as the release film of the pressure-sensitive adhesive sheet with the release film.
a release film and a member for constituting an image display device having a step with a height difference of 2 ⁇ m or more on the laminated surface are laminated via the present adhesive sheet, and the present adhesive is passed through the release film from the release film side.
the laminate can be produced by irradiating the sheet with active energy rays.
the irradiation dose of the active energy rays is preferably 4000 mJ/cm 2 or less, particularly 3500 mJ/cm 2 or less, further preferably 3200 mJ/cm 2 or less, from the viewpoint of step absorption.
it is preferably 2000 mJ/cm 2 or more, more preferably 2500 mJ/cm 2 or more, and even more preferably 2800 mJ/cm 2 or more.
a laminate for an image display device according to an example of the embodiment of the present invention (hereinafter sometimes referred to as "this laminate") is provided with an image display device constituent member on at least one side of the above-described present pressure-sensitive adhesive sheet. It is a laminated body.
the laminate includes a first image display device constituent member (hereinafter sometimes referred to as “first member”), the present pressure-sensitive adhesive sheet, and a second image display device constituent member (hereinafter sometimes referred to as “second member”). (sometimes referred to as “members”) are preferably laminated in this order. Further, the first member, the second member and the third image display device constituting member (hereinafter sometimes referred to as “third member”) are laminated in this order with the adhesive sheet interposed therebetween. It may also be a laminated body having a different configuration. Two or more members to be laminated may be the same or different.
the thickness of the laminate is not particularly limited.
the laminate when used in an image display device, the laminate is in the form of a sheet, and if the thickness is 0.02 mm or more, the handleability is good, and the thickness is 1.0 mm or less. If it is, it can contribute to thickness reduction of a laminated body. Therefore, the thickness of the laminate is preferably 0.02 mm or more, more preferably 0.03 mm or more, particularly 0.05 mm or more.
the upper limit is preferably 1.0 mm or less, more preferably 0.7 mm or less, particularly 0.5 mm or less.
the present laminate can be produced by attaching the present adhesive sheet to the first member, the second member and/or the third member. However, it is not limited to such a manufacturing method.
the first member, the second member, and the third member include, for example, A cover lens, a polarizing plate, a retardation film, a barrier film, a touch sensor film, a light emitting element, a PSA and the like can be mentioned.
the first member preferably has a touch input function.
the second member to the third member may have a touch input function.
at least one of the members may have various irregularities formed by wiring, printing, pattern development, surface treatment, embossing, etc. on the contact surface with the pressure-sensitive adhesive sheet.
the height difference of the unevenness is preferably 2 ⁇ m or more, for example, 2 ⁇ m or more and 10 ⁇ m or less, more preferably 8 ⁇ m or less, and more preferably 3 ⁇ m or more or 7 ⁇ m or less. is more preferable, and among them, 4 ⁇ m or more or 6 ⁇ m or less is more preferable.
At least one of the members for forming an image display device (including the first member, the second member, and the third member) to be laminated is made of urethane resin, cycloolefin resin, triacetylcellulose resin, (meta) It may be a resin sheet or a thin film glass mainly composed of one or more resins selected from the group consisting of acrylate resins, epoxy resins and polyimide resins.
the term "main component” refers to a component that accounts for the largest mass ratio among the components constituting the image display device constituent member, and specifically, the image display device constituent member or the member forming the member. It accounts for 50% by mass or more of the pressure-sensitive adhesive composition, more preferably 55% by mass or more, and more preferably 60% by mass or more.
This adhesive sheet can be hot-melted after being cured by active energy rays. With such a hot melt, even if the adherend surface of the adherend has unevenness, it can be laminated so as to follow the unevenness and absorb the unevenness, and the surface can be smoothed. . Therefore, when two image display device constituent members are bonded via the present pressure-sensitive adhesive sheet, even if one or both of the image display device constituent members are members that do not transmit light, the unevenness can be absorbed. Two members for forming an image display device can be pasted together.
This image display device> Forming a flexible image display device (also referred to as "present image display device") comprising this laminate by incorporating this laminate, for example, by laminating this laminate on another image display device constituent member. can be done.
a flexible image display device leaves no trace of bending even after repeated bending, bending, or winding operations, and can be bent, bent, or wound up when the bending, bending, or winding state is released. It is an image display device that can quickly recover to the state before the display and can display an image without distortion.
the laminate conforms to and absorbs unevenness having a height difference of 2 ⁇ m or more on the contact surface of the constituent member of the image display device with the adhesive sheet so as not to generate air bubbles.
a display device can be manufactured.
the present pressure-sensitive adhesive sheet can be placed on the viewing side of an image display panel such as a liquid crystal panel, or can be placed on the side opposite to the viewing side of the image display panel, that is, on the light source side. can.
the present laminate can be produced by a method for producing a laminate for an image display device including the following steps 1 to 3 and, if necessary, step 4.
Step 1 One surface of the pressure-sensitive adhesive sheet is attached to the member 1 for constituting an image display device.
Step 2 The pressure-sensitive adhesive sheet is cured by irradiation with active energy rays.
Step 3 The image display device constituting member 2 is adhered to the other surface of the pressure-sensitive adhesive sheet to form a laminate.
Step 4 The laminate is heat-treated to hot-melt the pressure-sensitive adhesive sheet.
Step 2 may be carried out after Step 1, or Step 1 may be carried out after Step 2. After performing steps 1 and 2, step 3 is performed.
Step 1 is a step of bonding one surface of the pressure-sensitive adhesive sheet to the member 1 for constituting an image display device.
a lamination method known methods such as roll lamination, press lamination using a parallel plate, and diaphragm lamination can be used.
the lamination environment there are an air lamination method in which lamination is performed under normal pressure and a vacuum lamination method in which lamination is performed under reduced pressure. From the viewpoint of preventing air bubbles during lamination, a method of laminating with a parallel plate under a reduced pressure environment is preferable. Moreover, you may adjust bonding temperature suitably.
Step 2 is a step of curing the adhesive sheet by irradiating it with active energy rays.
active energy rays ultraviolet rays and visible rays are suitable.
the light source when irradiating the active energy ray it is possible to use properly according to the wavelength and irradiation amount of the light to be irradiated from, for example, a high-pressure mercury lamp, a metal halide lamp, a xenon lamp, a halogen lamp, an LED lamp, a fluorescent lamp, etc. can.
irradiation time and irradiation means are not particularly limited, for example, in the case of ultraviolet irradiation, it is preferable to irradiate so that the integrated light amount at a wavelength of 365 nm is 2000 mJ/cm 2 or more, particularly 3000 mJ/cm 2 or more.
the present pressure-sensitive adhesive sheet is hot-melted. can absorb the step by following the step, and preferably the surface of the laminate can be smoothed.
Step 3 is a step of laminating the member 2 for constituting an image display device to the other surface of the pressure-sensitive adhesive sheet that has undergone steps 1 and 2 to form a laminate.
the image display device-constituting member 1 and/or the image display device-constituting member 2 may be heated and the image display device-constituting member 2 may be bonded together as needed.
the heating at this time is performed, for example, by applying a press plate heated to a predetermined temperature to a laminate for an image display device composed of image display device constituent member 1/adhesive sheet/image display device constituent member 2 from both sides.
a method of applying pressure can be mentioned.
the heating temperature at this time is preferably 50° C. or higher and 80° C. or lower. That is, the image display device constituent member 1 and/or the image display device constituent member 2 are heated to 50° C. or more and 80° C. or less to hot-melt the adhesive sheet, and the image display device constituent member 2 is bonded. is preferred.
the press pressure when pressing with the press plate is preferably 0.01 MPa or more or 0.4 MPa or less, more preferably 0.02 MPa or more or 0.35 MPa or less.
Step 4 is a step of heat-treating the laminated body obtained in Step 3 to hot-melt the pressure-sensitive adhesive sheet. This step 4 may be performed as required.
the surface of the first member or the second member for example, the surface to be laminated, has a height difference of 2 ⁇ m or more, for example, 2 ⁇ m or more and 10 ⁇ m or less. Even if the adhesive sheet has unevenness having a level difference, the pressure-sensitive adhesive sheet can follow the level difference and absorb the level difference, thereby smoothing the surface.
the heating temperature for the heat treatment of the laminate is preferably 40° C. or higher and 90° C. or lower. Above all, the temperature is preferably 50° C. or higher or 80° C. or lower, more preferably 60° C. or higher or 70° C. or lower.
an air pressure of 0.2 MPa or more and 0.8 MPa or less may be applied to the laminate for 5 minutes or more. At this time, the atmospheric pressure is preferably 0.2 MPa or more and 0.8 MPa or less, more preferably 0.4 MPa or more or 0.6 MPa or less.
the treatment time is preferably 5 minutes or more or 60 minutes or less, more preferably 10 minutes or more or 30 minutes or less.
a press pressure of 0.01 MPa or more and 0.4 MPa or less may be applied to the laminate in combination with the heat treatment.
the pressing pressure is preferably 0.01 MPa or more or 0.4 MPa or less, more preferably 0.02 MPa or more or 0.35 MPa or less.
the treatment time is preferably 5 seconds or more or 10 minutes or less, more preferably 10 seconds or more or 5 minutes or less.
the hot-melt treatment is preferably performed within 30 minutes after irradiating the adhesive sheet with active energy rays. The reason for this is that if the hot-melt treatment is performed before the adhesive is completely cured, it becomes easier to follow the unevenness having a level difference of 2 ⁇ m or more. From this point of view, the time from the irradiation of the active energy ray to the hot-melt treatment is preferably within 30 minutes, more preferably within 20 minutes, and even more preferably within 10 minutes.
the term “film” includes the “sheet”
the term “sheet” includes the “film”.
the expression “panel” such as an image display panel, a protective panel, etc. includes a plate, a sheet and a film.
(Meth)acrylic polymer (A-1) 6 parts by mass of polymethyl methacrylate macromonomer (Tg 105°C) having a number average molecular weight of 2800, 90 parts by mass of butyl acrylate (Tg -55°C), and acrylic acid ( Tg 106° C.) 4 parts by mass of acrylic graft copolymer (mass average molecular weight: 220,000, Tg ⁇ 45° C.) -
the glass transition temperature of each copolymer component in the (meth)acrylic polymer is the literature value of the glass transition temperature obtained from the homopolymer of the component.
the macromonomer the literature value of the glass transition temperature obtained from the homopolymer of the component forming the high-molecular-weight skeleton in the macromonomer was used.
the glass transition temperature of the acrylic copolymer the theoretical Tg calculated by the Fox calculation formula is described from the glass transition temperature and the composition ratio of each component of the copolymer.
⁇ Crosslinking agent (B)> ⁇ Crosslinking agent (B-1): propoxylated pentaerythritol triacrylate
the sheet-shaped pressure-sensitive adhesive composition a release film having a thickness of 75 ⁇ m (PET film manufactured by Mitsubishi Chemical Corporation) that has been subjected to silicone release treatment is laminated to form a laminate, and the release film/ A pressure-sensitive adhesive sheet 1 with a release film composed of pressure-sensitive adhesive sheet 1/release film was obtained.
the adhesive sheet 1 was an active energy ray-curable adhesive sheet having an active energy ray-curable adhesive sheet that is cured by irradiation with an active energy ray.
Adhesive sheet 2 and adhesive sheet 2 with a release film composed of release film/adhesive sheet 2/release film were produced in the same manner as in Example 1, except that the thickness was changed as shown in Table 1.
the adhesive sheet 2 was an active energy ray-curing adhesive sheet that was cured by irradiation with light.
Example 3 Each component was prepared as shown in Table 1 and used as a raw material for the pressure-sensitive adhesive layer.
the pressure-sensitive adhesive composition was applied to a release film of 100 ⁇ m (PET film manufactured by Mitsubishi Chemical Corporation, thickness 100 ⁇ m) and a release film of 75 ⁇ m (Mitsubishi Chemical Corporation).
PET film that is, sandwiched between two release films, hot-melt molded into a sheet with a thickness of 50 ⁇ m, and release film/adhesive sheet 3/release film-attached adhesive sheet 3 consisting of release film got
the adhesive sheet 3 was an active energy ray-curing adhesive sheet that was cured by irradiation with light.
Example 4 Each component was prepared as shown in Table 1 and used as a raw material for the pressure-sensitive adhesive layer.
Adhesive sheet 4 and adhesive sheet 4 with a release film composed of release film/adhesive sheet 4/release film were prepared in the same manner as in Example 3.
the adhesive sheet 4 was an active energy ray-curing adhesive sheet that was cured by irradiation with light.
Example 5 Each component was prepared as shown in Table 1 and used as a raw material for the pressure-sensitive adhesive layer.
Adhesive sheet 5 and adhesive sheet 5 with a release film composed of release film/adhesive sheet 5/release film were prepared in the same manner as in Example 1.
the adhesive sheet 5 was an active energy ray-curing adhesive sheet that was cured by irradiation with light.
Example 6 Each component was prepared as shown in Table 1 and used as a raw material for the pressure-sensitive adhesive layer.
Adhesive sheet 6 and adhesive sheet 6 with a release film composed of release film/adhesive sheet 6/release film were prepared in the same manner as in Example 3.
the adhesive sheet 6 was an active energy ray-curing adhesive sheet that was cured by irradiation with light.
Example 7 Each component was prepared as shown in Table 1 and used as a raw material for the pressure-sensitive adhesive layer.
Adhesive sheet 7 and adhesive sheet 7 with a release film composed of release film/adhesive sheet 7/release film were prepared in the same manner as in Example 3.
the adhesive sheet 7 was an active energy ray-curing adhesive sheet that was cured by irradiation with light.
a release film having a thickness of 75 ⁇ m (PET film manufactured by Mitsubishi Chemical Corporation) subjected to silicone release treatment is laminated to form a laminate, and a metal halide lamp irradiation device is formed.
a metal halide lamp irradiation device (Ushio Denki, UVC-0516S1, lamp UVL-8001M3-N) was applied to the pressure-sensitive adhesive composition through the release film so that the cumulative irradiation dose at a wavelength of 365 nm was 3000 mJ/cm 2 . Irradiation was performed to obtain a pressure-sensitive adhesive sheet laminate in which release films were laminated on both front and back sides of a 25 ⁇ m pressure-sensitive adhesive sheet (adhesive sheet 8).
the adhesive sheet 8 is an adhesive sheet in which the reaction due to light irradiation has progressed sufficiently and there is almost no room for active energy ray curing.
the pressure-sensitive adhesive composition was applied to a release film of 100 ⁇ m (PET film manufactured by Mitsubishi Chemical Corporation, thickness 100 ⁇ m) and a release film of 75 ⁇ m (Mitsubishi Chemical Corporation).
PET film that is, sandwiched between two release films, hot-melt molded into a sheet with a thickness of 25 ⁇ m, and release film/adhesive sheet 9/release film-attached adhesive sheet 9 consisting of release film got
the adhesive sheet 9 was an active energy ray-curing adhesive sheet that was cured by irradiation with light.
⁇ Creep test> The release film was removed from the release film-attached pressure-sensitive adhesive sheets prepared in Examples and Comparative Examples, and the stacking was repeated with a hand roller so that the thickness was about 0.9 mm.
a pressure-sensitive adhesive sheet with a release film was produced by punching into a shape, and this was used as a sample.
the release film was removed when installed in a rheometer ("DHR-2" manufactured by TA Instruments), and the measurement jig was a parallel plate with a diameter of 8 mm, temperature: 25 ° C., pressure: 1000 Pa. , the strain (creep strain) (%) after 3600 seconds was measured.
the pressure-sensitive adhesive sheets prepared in Examples and Comparative Examples were examined with an integrated amount of light at 365 nm of 3000 mJ/cm 2 for the pressure-sensitive adhesive sheets 1 to 4 and 6-7, and 4000 mJ/cm 2 for the pressure-sensitive adhesive sheets 5 and 9.
the adhesive sheet was irradiated with ultraviolet rays through the release film to cure the adhesive sheet.
the adhesive sheet 8 produced in Comparative Example 1 is an adhesive sheet in which the reaction due to light irradiation has progressed sufficiently and there is almost no room for active energy ray curing. did.
the adhesive sheets after curing were laminated to a thickness of about 0.9 mm, and a circle with a diameter of 8 mm was punched out and used as a sample.
a rheometer (DHR-2" manufactured by TA Instruments) measuring jig: diameter 8 mm parallel plate, temperature: 80 ° C., pressure: 1000 Pa, strain after 180 seconds (creep strain ) (%) was measured.
the integrated light quantity at 365 nm was 3000 mJ/cm 2 for adhesive sheets 1 to 4 and 6 to 7, and for adhesive sheets 5 and 9.
the adhesive sheet was irradiated with ultraviolet rays through the release film so as to be 4000 mJ/cm 2 to cure the adhesive sheet.
the adhesive sheet 8 produced in Comparative Example 1 is an adhesive sheet in which the reaction due to light irradiation has progressed sufficiently and there is almost no room for active energy ray curing. did.
the adhesive sheets after curing were laminated so as to have a thickness of about 0.9 mm, and a circle with a diameter of 8 mm was punched out and used as a sample.
a rheometer (“DHR-2" manufactured by TA Instruments Co., Ltd., measuring jig: 8 mm diameter parallel plate) was used at a temperature of 25 ° C., and the shear strain as the initial strain (x) was 200%.
a shear stress was applied to the sample for 600 seconds. After that, the stress was released and the residual strain (y) was measured after 600 seconds had passed, and the recovery rate was obtained from the following formula.
the integrated light quantity at 365 nm was 3000 mJ/cm 2 for adhesive sheets 1 to 4 and 6 to 7, and for adhesive sheets 5 and 9.
the adhesive sheet was irradiated with ultraviolet rays through the release film so as to be 4000 mJ/cm 2 to cure the adhesive sheet.
the gel fraction after curing with active energy rays was obtained in the same manner as the gel fraction evaluation procedure described above.
the adhesive sheet 8 produced in Comparative Example 1 is an adhesive sheet in which the reaction due to light irradiation has progressed sufficiently and there is almost no room for active energy ray curing, so this is measured as the gel fraction after curing. provided.
⁇ Adhesive strength> One of the release films was removed from the pressure-sensitive adhesive sheets with release films prepared in Examples and Comparative Examples, and a polyethylene terephthalate film ("Cosmo Shine A4300" manufactured by Toyobo Co., Ltd., thickness 100 ⁇ m) was applied as a backing film to a hand roller. and roll crimped. This was cut into strips of 10 mm width ⁇ 150 mm length, the remaining release film was peeled off, and the exposed adhesive surface was roll-bonded to soda lime glass using a hand roller. ° C., gauge pressure of 0.2 MPa, 20 minutes), and finished adhesion was performed to prepare an adhesive force measurement sample. At 23 ° C.
the backing film was peeled from the soda lime glass, the tensile strength was measured with a load cell, and the adhesive strength to the soda lime glass. (N/cm) was measured.
One of the release films was removed from the pressure-sensitive adhesive sheets with release films prepared in Examples and Comparative Examples, and a polyethylene terephthalate film ("Cosmo Shine A4300" manufactured by Toyobo Co., Ltd., thickness 100 ⁇ m) was applied as a backing film to a hand roller. and roll crimped. This was cut into strips of 10 mm width ⁇ 150 mm length, the remaining release film was peeled off, and the exposed adhesive surface was roll-bonded to soda lime glass using a hand roller. ° C., gauge pressure of 0.2 MPa, 20 minutes) to finish pasting.
the pressure-sensitive adhesive sheets were placed through a backing film so that the integrated amount of light at 365 nm was 3000 mJ/cm 2 for pressure-sensitive adhesive sheets 1 to 4 and 6-7, and 4000 mJ/cm 2 for pressure-sensitive adhesive sheets 5 and 9. was irradiated with ultraviolet rays to cure the adhesive sheet, and an adhesive force measurement sample was produced.
the backing film was peeled off from the soda lime glass while being pulled at an angle of 180° at a peeling speed of 300 mm/min, and the tensile strength was measured with a load cell.
the 180° peel strength (N/cm) of the sheet against soda lime glass was measured and taken as adhesive strength (curing after lamination).
the pressure-sensitive adhesive sheet 8 produced in Comparative Example 1 was not subject to this measurement because the reaction due to light irradiation had sufficiently progressed and there was almost no room for active energy ray curing.
the adhesive sheet cured as described above was cut into strips with a width of 10 mm and a length of 150 mm, and the remaining release film was peeled off.
This laminate was subjected to an autoclave treatment (60° C., gauge pressure 0.2 MPa, 20 minutes) and then finished and adhered to prepare an adhesive force measurement sample.
the backing film was peeled off from the soda lime glass while being pulled at an angle of 180° at a peeling speed of 300 mm/min, and the tensile strength was measured with a load cell.
the 180° peel strength (N/cm) of the sheet against soda lime glass was measured and taken as the adhesive strength (curing before lamination).
the pressure-sensitive adhesive sheet with a release film prepared in Examples and Comparative Examples was cut into a size of 5 cm ⁇ 5 cm, and the pressure-sensitive adhesive surface exposed by peeling one release film and the step of the evaluation substrate were provided.
the side surfaces are opposed to each other, vacuum lamination is performed under the conditions of a press pressure of 0.2 MPa for 30 seconds, and an autoclave treatment is performed under the conditions of 70 ° C. and an air pressure of 0.45 MPa for 20 minutes to prepare a laminate for step absorption evaluation. did.
the produced laminate was visually observed and evaluated according to the following evaluation criteria.
⁇ The pressure-sensitive adhesive sheet followed in the vicinity of all steps, and there were no air bubbles.
Good Two or less bubbles were generated near the step.
x The pressure-sensitive adhesive sheet did not follow the surface at three or more locations near the step, and air bubbles were generated.
the pressure-sensitive adhesive surface exposed by peeling off one release film of the pressure-sensitive adhesive sheet cured as described above is opposed to the surface of the side having a step of the evaluation substrate, and the press pressure is 0.2 MPa for 30 seconds.
Vacuum lamination was performed under the conditions of 70° C., atmospheric pressure of 0.45 MPa, and autoclave treatment for 20 minutes. The above procedure was performed within 10 minutes after the ultraviolet irradiation treatment to prepare a laminate for evaluation of step absorbability after curing. The produced laminate was visually observed and evaluated according to the same evaluation criteria as the step absorbability evaluation described above.
the integrated light quantity at 365 nm was 3000 mJ/cm for the adhesive sheets 1 to 4, 6 to 7 and the laminated sheet of Reference Example 1 for the adhesive sheets with release films prepared in Examples and Comparative Examples. 2.
the adhesive sheets 5 and 9 were cured by irradiating the adhesive sheets with ultraviolet rays through the release film so as to obtain 4000 mJ/cm 2 .
the adhesive sheet 8 produced in Comparative Example 1 is an adhesive sheet in which the reaction due to light irradiation has progressed sufficiently and there is almost no room for active energy ray curing.
each adhesive sheet was removed, and a transparent polyimide film (manufactured by Kolon Co., Ltd., thickness 50 ⁇ m) was rolled on both sides of the adhesive sheet with a hand roll. After that, autoclave treatment was performed under the conditions of 60° C., atmospheric pressure of 0.2 MPa, and 20 minutes to obtain a laminate sample for flexibility evaluation.
a transparent polyimide film manufactured by Kolon Co., Ltd., thickness 50 ⁇ m
the laminate sheet of Reference Example 1 was evaluated with the side of the adhesive sheet 5 as another adhesive sheet set inside. After being bent 200,000 times in a test environment of ⁇ 20° C. or 60° C. and 90% RH, evaluation was made according to the following evaluation criteria.
⁇ None of delamination, breakage, buckling, and flow occurred at the bent portion.
x Any of delamination, breakage, buckling, or flow occurred at the bent portion.
the laminate sample was bent at a radius of curvature R of 3 mm, stored at 60° C. and 90% RH for 24 hours, and then evaluated according to the following evaluation criteria.
the laminated sheet of Reference Example 1 was tested in a state in which the pressure-sensitive adhesive sheet 5 as another pressure-sensitive adhesive sheet was positioned inside and bent at a radius of curvature R of 3 mm.
⁇ None of delamination, breakage, buckling, and flow occurred at the bent portion.
x Any of delamination, rupture, buckling, or flow was observed at the bent portion.
Table 1 shows the results obtained by measuring and evaluating the adhesive sheet and laminate.
the pressure-sensitive adhesive sheets of Examples 1-7 exhibited good bonding properties in the step absorption test, excellent restorability, and exhibited excellent durability in the bending test when formed into a laminate. Furthermore, the pressure-sensitive adhesive sheets of Examples 1-4 exhibited good lamination properties in the level difference absorption test even when laminated after being cured. The pressure-sensitive adhesive sheet of Reference Example 1 also exhibited excellent step absorbability and excellent bending durability. On the other hand, the pressure-sensitive adhesive sheet produced in Comparative Example 1 used a material that did not have high fluidity, so the strain after 3,600 seconds at 25°C was 50% or less, and the step absorbability was poor. .
the pressure-sensitive adhesive sheet prepared in Comparative Example 2 uses a material with low flexibility after curing, so it has poor restorability after 200% deformation at 25 ° C after curing with active energy, and bending durability when used as a laminate. It was inferior in terms of sex.

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PCT/JP2021/048543 2021-01-27 2021-12-27 活性エネルギー線硬化性粘着シート、離型フィルム付き粘着シート、積層体、積層体の製造方法、積層シート、画像表示装置用積層体、フレキシブル画像表示装置，フレキシブルディスプレイ用粘着シートおよび画像表示装置用積層体の製造方法 WO2022163281A1 (ja)

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CN202180091745.1A CN116806245A (zh)	2021-01-27	2021-12-27	活性能量射线固化性粘合片、带脱模薄膜的粘合片、层叠体、层叠体的制造方法、层叠片、图像显示装置用层叠体、柔性图像显示装置、柔性显示器用粘合片和图像显示装置用层叠体的制造方法
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WO2023054218A1 (ja) *	2021-09-28	2023-04-06	三菱ケミカル株式会社	活性エネルギー線硬化性粘着シート、離型フィルム付き粘着シート積層体、画像表示装置構成用積層体、画像表示装置及び画像表示装置構成用積層体の製造方法
WO2024111438A1 (ja) *	2022-11-22	2024-05-30	三菱ケミカル株式会社	透明粘着シート、離型フィルム付き透明粘着シート、フレキシブル画像表示装置構成部材用透明粘着シート、画像表示装置用積層体及びフレキシブル画像表示装置

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