WO2009091225A2 - Composition for liquid crystal alignment layer, preparation method of liquid crystal alignment layer using the same, and optical film comprising the liquid crystal alignment layer - Google Patents
Composition for liquid crystal alignment layer, preparation method of liquid crystal alignment layer using the same, and optical film comprising the liquid crystal alignment layer Download PDFInfo
- Publication number
- WO2009091225A2 WO2009091225A2 PCT/KR2009/000272 KR2009000272W WO2009091225A2 WO 2009091225 A2 WO2009091225 A2 WO 2009091225A2 KR 2009000272 W KR2009000272 W KR 2009000272W WO 2009091225 A2 WO2009091225 A2 WO 2009091225A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- liquid crystal
- alignment layer
- acrylate
- crystal alignment
- meth
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 295
- 239000000203 mixture Substances 0.000 title claims abstract description 57
- 239000012788 optical film Substances 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000010408 film Substances 0.000 claims abstract description 159
- 239000000178 monomer Substances 0.000 claims abstract description 56
- 229920000642 polymer Polymers 0.000 claims abstract description 49
- 239000000758 substrate Substances 0.000 claims abstract description 48
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 94
- 150000001875 compounds Chemical class 0.000 claims description 68
- 239000000243 solution Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 17
- 230000001681 protective effect Effects 0.000 claims description 17
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical group [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 17
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 16
- -1 2-hydroxypropyl Chemical group 0.000 claims description 15
- 238000000576 coating method Methods 0.000 claims description 15
- 239000011248 coating agent Substances 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 14
- 229920000636 poly(norbornene) polymer Polymers 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 229920003023 plastic Polymers 0.000 claims description 8
- 239000004033 plastic Substances 0.000 claims description 8
- 229940114081 cinnamate Drugs 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 230000001678 irradiating effect Effects 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 claims description 4
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 claims description 4
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 4
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims description 4
- UZDMJPAQQFSMMV-UHFFFAOYSA-N 4-oxo-4-(2-prop-2-enoyloxyethoxy)butanoic acid Chemical compound OC(=O)CCC(=O)OCCOC(=O)C=C UZDMJPAQQFSMMV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims description 4
- ZMLXKXHICXTSDM-UHFFFAOYSA-N n-[1,2-dihydroxy-2-(prop-2-enoylamino)ethyl]prop-2-enamide Chemical compound C=CC(=O)NC(O)C(O)NC(=O)C=C ZMLXKXHICXTSDM-UHFFFAOYSA-N 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000007348 radical reaction Methods 0.000 claims description 3
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 claims description 2
- FYBFGAFWCBMEDG-UHFFFAOYSA-N 1-[3,5-di(prop-2-enoyl)-1,3,5-triazinan-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CN(C(=O)C=C)CN(C(=O)C=C)C1 FYBFGAFWCBMEDG-UHFFFAOYSA-N 0.000 claims description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 claims description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 2
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 claims description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- TZFOEYRGARRRGO-UHFFFAOYSA-N 2h-triazole-4,5-dicarboxylic acid Chemical compound OC(=O)C1=NNN=C1C(O)=O TZFOEYRGARRRGO-UHFFFAOYSA-N 0.000 claims description 2
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- PSSYEWWHQGPWGA-UHFFFAOYSA-N [2-hydroxy-3-[2-hydroxy-3-(2-hydroxy-3-prop-2-enoyloxypropoxy)propoxy]propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(O)COCC(O)COCC(O)COC(=O)C=C PSSYEWWHQGPWGA-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004386 diacrylate group Chemical group 0.000 claims description 2
- VKNUORWMCINMRB-UHFFFAOYSA-N diethyl malate Chemical compound CCOC(=O)CC(O)C(=O)OCC VKNUORWMCINMRB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- SMWNFFKPVLVOQQ-UHFFFAOYSA-N methyl 2-acetamidoprop-2-enoate Chemical compound COC(=O)C(=C)NC(C)=O SMWNFFKPVLVOQQ-UHFFFAOYSA-N 0.000 claims description 2
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 2
- MVBJSQCJPSRKSW-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]prop-2-enamide Chemical compound OCC(CO)(CO)NC(=O)C=C MVBJSQCJPSRKSW-UHFFFAOYSA-N 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- YWXLYZIZWVOMML-UHFFFAOYSA-N oxirane-2,2,3,3-tetracarbonitrile Chemical compound N#CC1(C#N)OC1(C#N)C#N YWXLYZIZWVOMML-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 2
- VOSUIKFOFHZNED-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,3,5-tricarboxylate Chemical compound C=CCOC(=O)C1=CC(C(=O)OCC=C)=CC(C(=O)OCC=C)=C1 VOSUIKFOFHZNED-UHFFFAOYSA-N 0.000 claims description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000005453 ketone based solvent Substances 0.000 claims 1
- 239000000853 adhesive Substances 0.000 abstract description 32
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 18
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
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- 238000006243 chemical reaction Methods 0.000 description 12
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- 230000003287 optical effect Effects 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 10
- 150000001925 cycloalkenes Chemical class 0.000 description 10
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 9
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- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 5
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 4
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Images
Classifications
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- 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
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- 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
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/56—Aligning agents
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- 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
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- 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
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- 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
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133528—Polarisers
-
- 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
-
- 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
- G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
- G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation
Abstract
Description
Claims (23)
- A composition for liquid crystal alignment layer, comprising1) one or more photoreactive polymer selected from the group consisting of a norbornene-based photoreactive polymer comprising a cinnamate group, a photoreactive polymer comprising an unit represented by the following Formula 1, and a photoreactive polymer comprising an unit represented by the following Formula 2,2) a multifunctional monomer crosslinkable with the 1) photoreactive polymer,3) a photoinitiator, and4) an organic solvent:[Formula 1][Formula 2]
- The composition for liquid crystal alignment layer according to claim 1, wherein the 1) photoreactive polymer has a number average molecular weight of 10,000 ~ 500,000.
- The composition for liquid crystal alignment according to claim 1, wherein the norbornene-based photoreactive polymer comprising a cinnamate group comprises a unit represented the following Formula 3:[Formula 3]wherein n is 50 to 5,000,at least one of R1 and R2 is represented by the following Formula 4, andthe other is selected from the group consisting of a hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms, and a group represented by the following Formula 4,[Formula 4]wherein R3 is each independently selected from the group consisting of a hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and an allyloxy group.
- The composition for liquid crystal alignment layer according to claim 1, wherein the norbornene-based photoreactive polymer comprising a cinnamate group comprises one or more selected from the group consisting of polynorbornene cinnamate, polynorbornene alkoxycinnamate (alkoxy group having 1 to 20 carbon atoms), polynorbornene allyloyloxycinnamate, polynorbornene fluorinatedcinnamate, polynorbornene chlorinatedcinnamate, and polynorbornene dicinnamate.
- The composition for liquid crystal alignment layer according to claim 1, wherein the norbornene-based photoreactive polymer comprising a cinnamate group comprises one or more selected from the units represented by the following Formulae 5 to 10:[Formula 5][Formula 6][Formula 7][Formula 8][Formula 9][Formula 10]wherein n is 50 to 5,000.
- The composition for liquid crystal alignment layer according to claim 1, wherein the content of the 1) photoreactive polymer is 0.1 to 20% by weight, based on the total composition for liquid crystal alignment layer.
- The composition for liquid crystal alignment layer according to claim 1, wherein the 2) multifunctional monomer comprises one or more selected from the group consisting of trimethylolpropane triacrylate, pentaerythritol tri(meth)/tetraacrylate, dipentaerythritol hexa/pentaacrylate, triglycerol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, pentaerythritol di(meth)acrylate, 1,6-hexandiol di(meth)acrylate, glycerol di(meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, methoxyethyl (meth)acrylate, N,N-dimethylaminoethyl (methyl)acrylate, butoxytriethylene glycol (meth)acrylate, 2-carboxyethyl acrylate, hydroxypropyl acrylate, mono-2-(acryloyloxy)ethyl succinate, vinyl acrylate, 3-(acryloyloxy)-2-hydroxypropyl (meth)acrylate, glycerol 1,3-diglycerolate diacrylate, tri(propylene glycol) glycerolate diacrylate, allyl (meth)acrylate, diacetone acrylamide, (meth)acrylamide, methyl 2-acetamidoacrylate, N-[tris(hydroxymethyl)methyl]acrylamide, N,N'-(1,2-dihydroxyethylene)bisacrylamide, N,N'-methylenebis(acrylamide), 1,3,5-triacryloylhexahydro-1,3,5-triazine, 2,4,6-triallyloxy-1,3,5-triazine, tris (2,3-epoxypropyl) isocyanurate, tris [2-(acryloyloxy)ethyl] isocyanurate, tetracyanoethylene oxide, triallyl 1,3,5-benzenetricarboxylate, diacetone acrylamide, N,N'-(1,2-dihydroxyethylene)bisacrylamide, poly(melamine-co-formaldehyde), 2-carboxyethyl acrylate, hydroxypropyl acrylate, mono-2-(acryloyloxy)ethyl succinate, vinyl acrylate, 3-(acryloyloxy)-2-hydroxypropyl (meth)acrylate, 2-(2-oxo-imidazolydinyl)ethyl (meth)acrylate, caprolactone 2-((meth)acryloyloxy)ethyl ester, mono-2-((meth)acryloyloxy)ethyl malate, 1,2,3-triazol-4,5-dicarboxylic acid, 3-allyloxy-1,2-propandiol, bis[4-(glycidyloxy)phenyl]methane, and 2-vinyl-1,3-dioxalene.
- The composition for liquid crystal alignment layer according to claim 1, wherein the content of the 2) multifunctional monomer is 0.1 to 20% by weight, based on the total composition for liquid crystal alignment layer.
- The composition for liquid crystal alignment layer according to claim 1, wherein the content of the 3) photoinitiator is 0.01 to 5% by weight, based on the total composition for liquid crystal alignment layer.
- The composition for liquid crystal alignment layer according to claim 1, wherein the 4) organic solvent includes one or more selected from the group consisting of ether-based, aromatic-based, halogen-based, olefin-based, and ketone-based solvents.
- A preparation method of liquid crystal alignment layer, comprising the steps of:1) applying and drying the composition for liquid crystal alignment layer according to any one of claims 1 to 11 on a substrate to form a coating, and2) irradiating UV rays onto the coating formed on the substrate.
- The preparation method according to claim 12, wherein the substrate of step 1) is a glass or plastic substrate.
- The preparation method according to claim 12, wherein the coating formed in step 1) has a thickness of 800 to 2,000Å.
- An optical film comprising the liquid crystal alignment layer prepared by the preparation method of liquid crystal alignment layer according to claim 12 and a polymeric liquid crystal compound.
- The optical film according to claim 15, wherein the polymeric liquid crystal compound includes one or more selected from substances an acrylate group being polymerizable by photoreaction.
- The optical film according to claim 16, wherein the substance an acrylate group is selected from the group consisting of cianobiphenyl-based acrylate, cianophenyl cyclohexane-based acrylate, cianophenyl ester-based acrylate, benzoic acid phenyl ester-based acrylate, phenyl pyrimidine-based acrylate, and mixtures thereof.
- A preparation method of optical film, comprising the steps of:1) applying and drying a liquid crystal compound solution comprising a polymeric liquid crystal compound, a photoinitiator, and an organic solvent on a liquid crystal alignment layer that is formed by using a composition for liquid crystal alignment layer according to any one of claims 1 to 11, and2) irradiating UV rays on the formed liquid crystal layer to form a liquid crystal film.
- The preparation method of optical film according to claim 18, wherein the content of the polymeric liquid crystal compound of step 1) is 5 to 70 parts by weight, based on 100 parts by weight of the total liquid crystal compound solution, and the content of the photoinitiator is 3 to 10 parts by weight, based on 100 parts by weight of the polymeric liquid crystal compound, in the total liquid crystal compound solution.
- The preparation method of optical film according to claim 18, wherein the solvent in the liquid crystal compound of step 1) includes one or more selected from the group consisting of halogenated hydrocarbons, aromatic hydrocarbons, ketones, alcohols, and cellosolves.
- A liquid crystal display device comprising one or more optical films accoriding to any one of claims 15 to 17.
- An integrated polarizing plate, comprising a polarizing film and one or more optical films of any one of claims 15 to 17 on one side or both sides of the polarizing film as a protective film.
- A liquid crystal display device comprising the integrated polarizing plate of claim 22.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/863,421 US8703253B2 (en) | 2008-01-18 | 2009-01-19 | Composition for liquid crystal alignment layer, preparation method of liquid crystal alignment layer using the same, and optical film comprising the liquid crystal alignment layer |
JP2010543062A JP5312482B2 (en) | 2008-01-18 | 2009-01-19 | Liquid crystal alignment film composition, method for producing liquid crystal alignment film using the same, and optical film including liquid crystal alignment film |
CN2009801025075A CN101918513B (en) | 2008-01-18 | 2009-01-19 | Composition for liquid crystal alignment layer, preparation method of liquid crystal alignment layer using the same, and optical film comprising the liquid crystal alignment layer |
US14/209,841 US20140192299A1 (en) | 2008-01-18 | 2014-03-13 | Composition for liquid crystal alignment layer, preparation method of liquid crystal alignment layer using the same, and optical film comprising the liquid crystal alignment layer |
US14/212,408 US20140199498A1 (en) | 2008-01-18 | 2014-03-14 | Composition for liquid crystal alignment layer, preparation method of liquid crystal alignment layer using the same, and optical film comprising the liquid crystal alignment layer |
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US14/209,841 Division US20140192299A1 (en) | 2008-01-18 | 2014-03-13 | Composition for liquid crystal alignment layer, preparation method of liquid crystal alignment layer using the same, and optical film comprising the liquid crystal alignment layer |
US14/212,408 Division US20140199498A1 (en) | 2008-01-18 | 2014-03-14 | Composition for liquid crystal alignment layer, preparation method of liquid crystal alignment layer using the same, and optical film comprising the liquid crystal alignment layer |
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JP (1) | JP5312482B2 (en) |
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-
2009
- 2009-01-19 US US12/863,421 patent/US8703253B2/en active Active
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- 2009-01-19 CN CN2009801025075A patent/CN101918513B/en active Active
- 2009-01-19 KR KR1020090004159A patent/KR101057627B1/en active IP Right Grant
- 2009-01-19 JP JP2010543062A patent/JP5312482B2/en active Active
-
2014
- 2014-03-13 US US14/209,841 patent/US20140192299A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
---|---|
US8703253B2 (en) | 2014-04-22 |
CN101918513A (en) | 2010-12-15 |
JP5312482B2 (en) | 2013-10-09 |
KR20090079842A (en) | 2009-07-22 |
JP2011510345A (en) | 2011-03-31 |
WO2009091225A3 (en) | 2009-10-29 |
US20140199498A1 (en) | 2014-07-17 |
US20110043731A1 (en) | 2011-02-24 |
US20140192299A1 (en) | 2014-07-10 |
KR101057627B1 (en) | 2011-08-19 |
CN101918513B (en) | 2013-05-08 |
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