JPWO2018088558A1 - 赤外波長域用染料系偏光板 - Google Patents
赤外波長域用染料系偏光板 Download PDFInfo
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- JPWO2018088558A1 JPWO2018088558A1 JP2018550297A JP2018550297A JPWO2018088558A1 JP WO2018088558 A1 JPWO2018088558 A1 JP WO2018088558A1 JP 2018550297 A JP2018550297 A JP 2018550297A JP 2018550297 A JP2018550297 A JP 2018550297A JP WO2018088558 A1 JPWO2018088558 A1 JP WO2018088558A1
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- Prior art keywords
- dye
- polarizing plate
- film
- infrared
- absorption
- Prior art date
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 4
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
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- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical group C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- AOMZHDJXSYHPKS-UHFFFAOYSA-L disodium 4-amino-5-hydroxy-3-[(4-nitrophenyl)diazenyl]-6-phenyldiazenylnaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(N=NC=3C=CC=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 AOMZHDJXSYHPKS-UHFFFAOYSA-L 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
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- 239000001257 hydrogen Substances 0.000 description 2
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- 229910052742 iron Inorganic materials 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
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- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical compound N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 2
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- 229910052763 palladium Inorganic materials 0.000 description 2
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
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- 239000004800 polyvinyl chloride Substances 0.000 description 2
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- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical group C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical group C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical class [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 1
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- 241000694440 Colpidium aqueous Species 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010042674 Swelling Diseases 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
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- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 229910052787 antimony Inorganic materials 0.000 description 1
- GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical class F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- AMTXUWGBSGZXCJ-UHFFFAOYSA-N benzo[e][1,3]benzoselenazole Chemical group C1=CC=C2C(N=C[se]3)=C3C=CC2=C1 AMTXUWGBSGZXCJ-UHFFFAOYSA-N 0.000 description 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical group C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
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- 239000012461 cellulose resin Substances 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
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- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
- 125000006841 cyclic skeleton Chemical group 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
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- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
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- 229910052738 indium Inorganic materials 0.000 description 1
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- 229960004657 indocyanine green Drugs 0.000 description 1
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- 229910001507 metal halide Inorganic materials 0.000 description 1
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- 150000002739 metals Chemical class 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
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- 238000000465 moulding Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 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
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- WKFBZNUBXWCCHG-UHFFFAOYSA-N phosphorus trifluoride Chemical class FP(F)F WKFBZNUBXWCCHG-UHFFFAOYSA-N 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0083—Solutions of dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
-
- G—PHYSICS
- G02—OPTICS
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- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
- G02B5/3041—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks
- G02B5/305—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks including organic materials, e.g. polymeric layers
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
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- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
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- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/086—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines more than five >CH- groups
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- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/50—Tetrazo dyes
- C09B35/56—Tetrazo dyes of the type
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- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
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- C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
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Abstract
Description
(1) 赤外域に吸収を有する染料を含有する延伸されたフィルムであって、該フィルムが赤外域において二色性を有する偏光板。
(2) 前記染料の最大吸収波長が700〜1500nmにある(1)に記載の偏光板。
(3) 前記染料が、アゾ化合物、アンスラキノン化合物、及びシアニン化合物からなる群より選択される(1)又は(2)に記載の偏光板。
(4) 前記染料が、水溶性染料である(1)〜(3)のいずれかに記載の偏光板。
(5) 前記フィルムの基材が親水性高分子である(1)〜(4)のいずれかに記載の偏光板。
(6) 前記親水性高分子が、ポリビニルアルコール系樹脂である(5)に記載の偏光板。
(7) 片面又は両面に透明保護層を備える(1)〜(6)のいずれかに記載の偏光板。
(8) (1)〜(7)のいずれかに記載の偏光板を備える液晶表示装置、センサ、レンズ、スイッチング素子、アイソレータ、又はカメラ。
(9) 赤外域に吸収を有する染料の、フィルムに含有され、該フィルムを延伸することによって二色性を発現させた偏光板への使用方法。
(10) 前記染料の最大吸収波長が700〜1500nmにある(9)に記載の使用方法。
(11) 前記染料が、アゾ化合物、アンスラキノン化合物、及びシアニン化合物からなる群より選択される(9)又は(10)に記載の使用方法。
(12) 前記染料が、水溶性染料である(9)〜(11)のいずれかに記載の使用方法。
(13) 前記偏光板が液晶表示装置、センサ、レンズ、スイッチング素子、アイソレータ、又はカメラ用である、(9)〜(12)のいずれかに記載の使用方法。
なお、X1〜X4が窒素原子の場合、その窒素原子は、水素付加体であるNH、あるいは炭素数1〜4のアルキル基、置換基を有しても良いフェニル基等で置換された窒素原子であっても良い。
ケン化度99%以上の平均重合度2400のポリビニルアルコールフィルム(クラレ社製 VF−PS)を40℃の温水に3分浸漬し、膨潤処理を適用し延伸倍率を1.30倍とした。水を1500質量部、トリポリリン酸ナトリウムを1.5質量部、無水芒硝を1.5質量部、赤外域に吸収を有するシアニン染料として式(1)に示されるFEW CHEMICAL社製 S2180を1.5質量部含有している45℃の染色液に、膨潤したフィルムを8分00秒間浸漬して、フィルムにアゾ化合物を含有させた。得られたフィルムを、ホウ酸(Societa Chimica Larderello s.p.a.社製)20g/lを含有した40℃の水溶液に1分浸漬した。浸漬後のフィルムを、5.0倍に延伸しながら、ホウ酸30.0g/lを含有した50℃の水溶液中で5分間の延伸処理を行った。得られたフィルムを、その緊張状態を保ちつつ、25℃の水に20秒間浸漬させることにより洗浄処理した。洗浄後のフィルムを70℃で9分間乾燥させ、偏光板を得た。この偏光板に対して、ポリビニルアルコール(日本酢ビポバール社製 NH−26)を4%で水に溶解したものを接着剤として用いて、アルカリ処理したトリアセチルセルロースフィルム(富士写真フィルム社製 TD−80U)をラミネートして保護フィルムを設けた偏光板を得た。得られた偏光板は保護フィルムを設ける前と同じ光学特性を有し、特に単体透過率、色相、偏光度等を維持していた。この偏光板を実施例1の測定試料とした。
実施例1において、用いた赤外域に吸収を有する染料として、シアニン系染料である式(2)に示されるFEW CHEMICAL社製 S0378(1.5質量部)に替えた以外は同様にして、偏光板を作製し、測定試料とした。
実施例1において、用いた赤外域に吸収を有する染料として、アゾ系染料であるオリヱント化学工業社製 C.I.Acid Black 2(1.5質量部)に替えた以外は同様にして、偏光板を作製し、測定試料とした。
実施例1において、用いた赤外域に吸収を有する染料として、式(3)に示されるアゾ系染料であるSHAOXING BIYING TEXITILE TECHNOLOGY Co., LTD社製 C.I.Direct Black 19(1.5質量部)に替えた以外は同様にして、偏光板を作製し、測定試料とした。
東洋紡社製 バイロンUR8200 100質量部に、赤外域に吸収を有するシアニン染料として式(4)で示されるFEW CHEMICAL社製 S0391を0.15質量部含有させ、十分に混合させた組成物を、ガラス上に250μmの厚みでキャストした。キャスト後に、バイロンUR8200中に含まれていた溶媒を乾燥したところ、75μmのフィルムを得た。得られたフィルムを80℃の環境下で、元の長さに対して3倍に延伸して、偏光板を得た。
東洋紡社製 バイロンUR1400 100質量部に、赤外域に吸収を有するシアニン染料として式(5)で示されるFEW CHEMICAL社製 S2437を0.15質量部含有させ、十分に混合させた組成物を、ガラス上に250μmの厚みでキャストした。キャスト後に、バイロンUR1400中に含まれていた溶媒を乾燥したところ、75μmのフィルムを得た。得られたフィルムを80℃の環境下で、元の長さに対して3倍に延伸して、偏光板を得た。
東洋紡社製 バイロンUR1400 100質量部に、赤外域に吸収を有するアンスラキノン染料として式(6)で示される特開昭59−26293 化合物番号19を0.2質量部含有させ、十分に混合させた組成物を、ガラス上に250μmの厚みでキャストした。キャスト後に、バイロンUR1400中に含まれていた溶媒を乾燥したところ、75μmのフィルムを得た。得られたフィルムを80℃の環境下で、元の長さに対して3倍に延伸して、偏光板を得た。
実施例3において、同様なBlack染料として、日本化薬社製 Black S(1.5質量部)に替えた以外は同様にして、偏光板を作製し、測定試料とした。
実施例1〜7及び比較例1で得られた測定試料の評価を次のようにして行った。
(a)偏光平行透過率Ky、及び偏光直交透過率Kz
各測定試料の偏光平行透過率Ky、及び、偏光直交透過率Kzを、分光光度計(日立製作所社製“UH−4150”)を用いて測定した。ここで偏光平行透過率Kyは、紫外〜赤外に対応したグランテーラー偏光子を介して光を測定試料に照射するに際し、グランテーラー偏光子の光の吸収軸と、測定試料をその吸収軸とが平行となるように重ね合せて測定した各波長の分光透過率である。偏光平行透過率Kzは、紫外〜赤外に対応したグランテーラー偏光子を介して光を測定試料に照射するに際し、グランテーラー偏光子の光の吸収軸と、測定試料をその吸収軸とが直交となるように重ね合せて測定した各波長の分光透過率である。
各測定試料のコントラストを、以下の式に、偏光平行透過率Ky及び偏光直交透過率Kzを代入して求めた。
コントラスト=Ky/Kz
実施例1〜7における測定試料を、90℃の耐熱試験、及び、65℃、相対湿度95%RHの環境に240時間に適用した。その結果、実施例1〜7の測定試料はコントラストや波長の変化は見られなかった。このことから、実施例1〜7の偏光板は信頼性が高く、かつ、これを用いた装置やレンズは信頼性の高い赤外域のコントラストを得ることが出来る。
Claims (13)
- 赤外域に吸収を有する染料を含有する延伸されたフィルムであって、該フィルムが赤外域において二色性を有する偏光板。
- 前記染料の最大吸収波長が700〜1500nmにある請求項1に記載の偏光板。
- 前記染料が、アゾ化合物、アンスラキノン化合物、及びシアニン化合物からなる群より選択される請求項1又は2に記載の偏光板。
- 前記染料が、水溶性染料である請求項1〜3のいずれか一項に記載の偏光板。
- 前記フィルムの基材が親水性高分子である請求項1〜4のいずれか一項に記載の偏光板。
- 前記親水性高分子が、ポリビニルアルコール系樹脂である請求項5に記載の偏光板。
- 片面又は両面に透明保護層を備える請求項1〜6のいずれか一項に記載の偏光板。
- 請求項1〜7のいずれか一項に記載の偏光板を備える液晶表示装置、センサ、レンズ、スイッチング素子、アイソレータ、又はカメラ。
- 赤外域に吸収を有する染料の、フィルムに含有され、該フィルムを延伸することによって二色性を発現させた偏光板への使用方法。
- 前記染料の最大吸収波長が700〜1500nmにある請求項9に記載の使用方法。
- 前記染料が、アゾ化合物、アンスラキノン化合物、及びシアニン化合物からなる群より選択される請求項9又は10に記載の使用方法。
- 前記染料が、水溶性染料である請求項9〜11のいずれか一項に記載の使用方法。
- 前記偏光板が液晶表示装置、センサ、レンズ、スイッチング素子、アイソレータ、又はカメラ用である、請求項9〜12のいずれか一項に記載の使用方法。
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