CA2439201A1 - Retardation films comprising a polymer film having a uv-curable resin composition for alignment film and a liquid crystalline compound - Google Patents

Retardation films comprising a polymer film having a uv-curable resin composition for alignment film and a liquid crystalline compound Download PDF

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Publication number
CA2439201A1
CA2439201A1 CA 2439201 CA2439201A CA2439201A1 CA 2439201 A1 CA2439201 A1 CA 2439201A1 CA 2439201 CA2439201 CA 2439201 CA 2439201 A CA2439201 A CA 2439201A CA 2439201 A1 CA2439201 A1 CA 2439201A1
Authority
CA
Canada
Prior art keywords
film
amended
meth
liquid crystalline
resin composition
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CA 2439201
Other languages
French (fr)
Other versions
CA2439201C (en
Inventor
Kouichi Tanaka
Syoushi Takahashi
Kenichiro Yoshioka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Kayaku Co Ltd
Polatechno Co Ltd
Original Assignee
Nippon Kayaku Kabushiki Kaisha
Kouichi Tanaka
Syoushi Takahashi
Kenichiro Yoshioka
Polatechno Co., Ltd.
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.)
Filing date
Publication date
Application filed by Nippon Kayaku Kabushiki Kaisha, Kouichi Tanaka, Syoushi Takahashi, Kenichiro Yoshioka, Polatechno Co., Ltd. filed Critical Nippon Kayaku Kabushiki Kaisha
Publication of CA2439201A1 publication Critical patent/CA2439201A1/en
Application granted granted Critical
Publication of CA2439201C publication Critical patent/CA2439201C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3083—Birefringent or phase retarding elements
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3016—Polarising elements involving passive liquid crystal elements
    • 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
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/02—Alignment layer characterised by chemical composition
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/05—Bonding or intermediate layer characterised by chemical composition, e.g. sealant or spacer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/05—Bonding or intermediate layer characterised by chemical composition, e.g. sealant or spacer
    • C09K2323/059—Unsaturated aliphatic polymer, e.g. vinyl
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/06—Substrate layer characterised by chemical composition
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/3188—Next to cellulosic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31909—Next to second addition polymer from unsaturated monomers
    • Y10T428/31928—Ester, halide or nitrile of addition polymer

Abstract

(1) There are provided a UV-curable resin composition for alignment film and an alignment film which is prepared by curing the composition with UV rays. (2) The migration of a material which is present in a polymer film and capable of affecting the optical properties of a liquid crystalline compound layer to the liquid crystalline compound layer is controlled or blocked.
(1) A UV-curable resin composition for alignment film comprising at least one (meth)acrylate compound having one or more polar groups and one or more (meth)acryloyl groups in the molecule and a photoinitiator; and an alignment film which is prepared by curing the composition with UV rays. (2) A protective layer inserted between a polymer film and a liquid crystalline compound layer for controlling or blocking the migration of a material, which is present in a polymer film and capable of affecting the optical properties of the liquid crystalline compound layer, to the liquid crystalline compound layer.

Claims (30)

1. (Amended) A retardation film comprising a liquid crystalline compound layer, a protective layer and a polymer film characterized in that the protective layer comprising a cured product of a UV-curable resin composition is inserted between the polymer film and the liquid crystalline compound layer to control or block the migration to the liquid crystalline compound layer of a material present in the polymer film and affecting the optical properties of the liquid crystalline compound layer by migrating to the liquid crystalline compound layer.
2. (Amended) The retardation film as defined in claim 1 wherein the UV-curable resin composition comprises at least one (meth)acrylate compound having one or more polar groups and one or more (meth)acryloyl groups in the molecule and a photoinitiator.
3. (Amended) The retardation film as defined in claim 2 wherein the polar group is any one of hydroxyl, ether, amino and urethane groups and an isocyanurate ring.
4. (Amended) The retardation film as defined in claim 2 or 3 wherein the UV-curable resin composition contains at least two of a (meth)acrylate compound having one or more polar groups and one (meth)acryloyl group in the molecule, a (meth)acrylate compound having one or more polar groups and two (meth)acryloyl groups in the molecule, and a (meth)acrylate compound having one or more polar groups and three or more (meth)acryloyl groups in the molecule.
5. (Amended) The retardation film as defined in any one of claims 1 to 4 characterized in that the UV-curable resin composition contains a leveling agent in an amount of 0.0001 part by weight or more and 0.005 parts by weight or less in 100 parts by weight of the UV-curable resin composition.
6. (Amended) The retardation film as defined in any one of claims 1 to 5 wherein the unreacted (meth)acrylate compound content is 0 part by weight or more and 5 parts by weight or less in 100 parts by weight of the resin composition after UV
curing.
7. (Deleted)
8. (Deleted)
9. (Deleted)
10. (Deleted)
11. (Deleted)
12. (Deleted)
13. (Deleted)
14. (Deleted)
15. (Deleted)
16. (Deleted)
17. (Amended) The retardation film as defined in any one of claims 1 to 6 characterized in that the protective layer is capable of aligning the liquid crystalline compound by rubbing.
18. (Amended) The retardation film as defined in claim 1 or 17 wherein the change in haze on the surface of the protective layer is 4 % or more and 70 % or less before and after an abrasion test using a Taber abrasion tester with abrader wheels for revolutions under a load of 500 g.
19. (Amended) The retardation film as defined in any one of claims 1 to 6 and 17 to 18 characterized in that the UV-curable resin composition used for the protective layer contains a (meth)acrylate compound comprising the reaction product of bisphenol A or a derivative thereof with (meth)acrylic acid.
20. (Amended) The retardation film as defined in any one of claims 1 to 6 and 17 to 19 characterized in that it has an alignment film for aligning the liquid crystalline compound on the protective layer.
21. (Amended) The retardation film as defined in claim 20 wherein the alignment film on the protective layer is a protective layer as defined in any one of claims 1 to 6 and 17 to 19.
22. (Amended) The retardation film as defined in any one of claims 1 to 6 and 17 to 19 wherein the polymer film is based on a cellulose derivative and further contains a plasticizer.
23. (Amended) The retardation film as defined in claim 22 wherein the cellulose derivative is triacetyl cellulose.
24. (Amended) A process for preparing a retardation film comprising applying a protective layer as defined in any one of claims 1 to 6 and 17 to 21 on a polymer film and overlaying a liquid crystalline compound layer thereon.
25. (Amended) A process for preparing a retardation film comprising applying a protective layer as defined in any one of claims 1 to 6 and 17 to 19 on a polymer film, overlaying an alignment film as defined in claim 20 or 21 thereon, and further overlaying a liquid crystalline compound layer thereon.
26. (Deleted)
27. (Deleted)
28. (Amended) An optical film obtained by laminating a polarizing film having a protective layer and a retardation film as defined in any one of claims 1 to 6 and 17 to 23 in such a manner that the protective layer side of the polarizing film and the liquid crystalline compound layer side of the retardation film are opposed to each other.
29. (Added) An alignment film comprising a cured film of a UV-curable resin composition layer obtained by forming the UV-curable resin composition layer on a substrate and curing it with UV rays and exhibiting the function of aligning a liquid crystalline compound layer formed on the surface of the alignment film by rubbing the surface of the alignment film wherein the change in haze on the surface of the alignment film is 0.5 % or more and 70 % or less before and after an abrasion test using a Taber abrasion tester with abrader wheels for 100 revolutions under a load of 500 g.
30. (Added) The alignment film as defined in claim 29 wherein the UV-curable resin composition comprises at least one (meth)acrylate compound having one or more polar groups and one or more (meth)acryloyl groups in the molecule and a photoinitiator and the unreacted (meth)acrylate compound content is 0 part by weight or more and 5 parts by weight or less in 100 parts by weight of the resin composition after UV curing.
CA2439201A 2001-02-23 2002-02-22 Retardation films comprising a polymer film having a uv-curable resin composition for alignment film and a liquid crystalline compound Expired - Fee Related CA2439201C (en)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
JP2001047575 2001-02-23
JP2001-47575 2001-02-23
JP2001-49696 2001-02-26
JP2001049696 2001-02-26
JP2001-123871 2001-04-23
JP2001123931 2001-04-23
JP2001123871 2001-04-23
PCT/JP2002/001608 WO2002067026A1 (en) 2001-02-23 2002-02-22 A phase difference film comprising polymer film having ultraviolet curable resin composition for alignment film and liquid crystalline compound
JP2001-123931 2005-04-23

Publications (2)

Publication Number Publication Date
CA2439201A1 true CA2439201A1 (en) 2002-08-29
CA2439201C CA2439201C (en) 2011-09-06

Family

ID=27482064

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2439201A Expired - Fee Related CA2439201C (en) 2001-02-23 2002-02-22 Retardation films comprising a polymer film having a uv-curable resin composition for alignment film and a liquid crystalline compound

Country Status (8)

Country Link
US (2) US7442420B2 (en)
EP (2) EP1372004B1 (en)
KR (2) KR100836140B1 (en)
CN (1) CN1291250C (en)
CA (1) CA2439201C (en)
HK (2) HK1057922A1 (en)
TW (1) TWI237132B (en)
WO (1) WO2002067026A1 (en)

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US7531223B2 (en) * 2004-12-28 2009-05-12 Dai Nippon Printing Co., Ltd. Optical element and method for manufacturing the same

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Also Published As

Publication number Publication date
US20050089650A1 (en) 2005-04-28
HK1105227A1 (en) 2008-02-06
TWI237132B (en) 2005-08-01
EP1813972B8 (en) 2012-11-21
WO2002067026A1 (en) 2002-08-29
KR100837237B1 (en) 2008-06-12
KR100836140B1 (en) 2008-06-09
EP1372004A1 (en) 2003-12-17
KR20030081459A (en) 2003-10-17
CN1291250C (en) 2006-12-20
CN1493007A (en) 2004-04-28
EP1372004B1 (en) 2011-05-11
HK1057922A1 (en) 2004-04-23
CA2439201C (en) 2011-09-06
KR20070120621A (en) 2007-12-24
US7445820B2 (en) 2008-11-04
US7442420B2 (en) 2008-10-28
US20060008663A1 (en) 2006-01-12
EP1813972A3 (en) 2008-04-02
EP1813972B1 (en) 2012-10-10
EP1372004A4 (en) 2006-11-29
EP1813972A2 (en) 2007-08-01

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