JP6141269B2 - 液晶色素混合物 - Google Patents
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- 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
- C09K19/60—Pleochroic dyes
- C09K19/606—Perylene dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
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- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/60—Pleochroic dyes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
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Description
と、吸収軸に垂直に伝わる光
との吸収における比である:
米国特許4378302号は、液晶ゲスト・ホスト混合物を形成するためのペリレンビスイミドと液晶との混合物を記載している。
[式中、
Ryはリレン族からの発色団であり、C1は第二の発色団であり、且つX1はRyとC1との間の共役を妨げるスペーサーである]
を有する基を含有する多重発色団(multichromophoric)色素であることを特徴とする、前記ゲスト・ホスト液晶色素混合物によって解決される。
A1−Ry−X1−C1−X2・・・−Cn−A2
[式中、
A1およびA2は可溶化脂肪族末端部であり、X1は共有結合スペーサー(リンカーとも称される)であり、且つ、Ciは発色団であり、且つ、Ryはリレン型の色素である]。さらに強化された可溶性のために、C1およびCnの単位は、非対称の分子が得られるように異なっていてよい。
本発明による混合物のための1つの適した二発色団色素は、2−(4−(2−(2,6−ジイソプロピルフェニル)−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[5,10]アントラ[2,1,9−def]イソキノリン−8−イル)フェニル)−9−(トリデカン−7−イル)アントラ[2,1,9−def:6,5,10−d’e’f’]ジイソキノリン−1,3,8,10(2H,9H)−テトラオン(PBI−PMI)であり、吸収軸沿いに配置する2つの発色団単位を示す。
8質量%の4’’−ペンチル−[1,1’:4’,1’’−ターフェニル]−4−カルボニトリル
25質量%の4’−ヘプチル−[1,1’−ビフェニル]−4−カルボニトリル
51質量%の4’−ペンチル−[1,1’−ビフェニル]−4−カルボニトリル
および16質量%の4’−(オクチルオキシ)−[1,1’−ビフェニル]−4−カルボニトリル。
4−プロピル−4’−(3,4,5−トリフルオロフェネチル)−1,1’−ビ(シクロヘキサン)、
・ 吸収における高い(>10)二色性比
・ 液晶中でのゲストの高い可溶性(>0.2質量%)、ひいては混合物の高い吸収率
・ 色素の高い光安定性を、
・ 良好な蛍光量子収率(>50%)と共に
もたらす。
例えば、文献US4378302号(Aftergut Siegfried et al)のとおり、単一発色団ペリレン色素を使用し、LC・色素混合物から出発することは、多重発色団ペリレンを単に選択するためには充分ではない。本願での手法と、リンカーが本願で記載されるものとは異なって選択される多重発色団ペリレン色素を使用したLC色素混合物とを比較するために、比較例を示す。
特許出願DE−A−102005037115号においては、異なる発色団が−Y’−A−Y−部分によってY=−O−または−S−と結合され(A=芳香族成分)、従って、上記で概説した要求には従わないフレキシブルリンカーを含有する。特定の例(図3)においては、2つのペリレン発色団がフレキシブルリンカーによって結合されている。図3内のグラフは、LCホスト中の化合物PDI−アルキル−PDIの吸収スペクトル(LC材料の配向に平行および垂直に偏光された光で測定)を示す。平行および垂直の測定について、吸収強度の差異は観察できず、このことは、LCによる色素の配列が生じていないことを示す。さらには、該化合物は可溶性が非常に悪かった(<0.75質量%)。
さらには、特許出願DE−A−102005037115号においては、1つの分子内の異なる発色団が線状に配置されておらず、それは、上述の−Y’−A−Y−部分によってもたらされる柔軟性に起因する。LC混合物中の2つの異なる多重発色団ペリレン色素の吸収スペクトルを、図4および5に示す。各々の場合において、LCホストの配向に平行または垂直に測定されたスペクトル間での差異は観察されず、このことは、多重発色団色紙の吸収軸が線状ではないことを立証する。ここでもまた、LCホストE7中での色素の可溶性は非常に乏しい(<0.75質量%)。
特許出願US4378302号内のような、単一発色団ペリレン色素の使用は、上記で概説された要求を明らかに満たさない。1つの例を図6に示す。前記のグラフは、LCホスト中の化合物1−PDIの吸収スペクトルを示す。平行および垂直に測定されたスペクトル間の吸収における差異は、この単一色素がLCホストにより配列することを示す。しかしながら、二色性比は約4であると計算され、それは上述の要求(DR>10)に合致しない。該化合物は、LCホストE7中で0.15質量%までの可溶性であった。
上記で示された否定的な例と対照させて、3つの異なる多重発色団棒状分子の吸収スペクトルを図7、8および9に示す。それらの全ては、LCホストE7中で高い可溶性(0.25質量%〜1質量%)を示し、且つ、高い二色性比を示し、従って、上記で概説された要求に合う。
Claims (8)
- ホストとしてのカラミチック且つサーモトロピック液晶と、ゲストとしての二色性蛍光色素とを含むゲスト・ホスト液晶色素混合物であって、前記二色性蛍光色素が、一般式
Ry−X1−C1
[式中、
Ryはリレン族からの発色団であり、C1は第二の発色団であり、且つX1はRyとC1との間の共役を妨げるスペーサーであり、且つ、前記スペーサーX1は、分子の長さ方向に垂直な軸上での曲げまたは折りたたみに対する剛性をもたらすように選択される]
を有する少なくとも1つの基を含有する多重発色団色素であり、前記多重発色団色素の発色団は線状に配置されていることを特徴とする、前記ゲスト・ホスト液晶色素混合物。 - 発色団の一次吸収軸が、ゲスト分子の長軸に沿って配置されている、請求項1に記載のゲスト・ホスト液晶色素混合物。
- 発色団C1の一次吸収軸が、発色団Ryの吸収軸に関して垂直に取り付けられている、請求項1に記載のゲスト・ホスト液晶色素混合物。
- 発色団RyとC1とが同一である、請求項1に記載のゲスト・ホスト液晶色素混合物。
- 照明、ディスプレイ、レージングまたは発光型太陽集光器用途における、請求項1から4までのいずれか1項に記載のゲスト・ホスト液晶色素混合物の使用。
- 前記色素が、延伸された葉巻型の形状を有する、請求項1から4までのいずれか1項に記載のゲスト・ホスト液晶色素混合物。
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Application Number | Priority Date | Filing Date | Title |
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EP11172744.2 | 2011-07-05 | ||
EP11172744 | 2011-07-05 | ||
PCT/EP2012/062868 WO2013004677A1 (en) | 2011-07-05 | 2012-07-03 | Liquid crystal dye mixture |
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JP2014527092A JP2014527092A (ja) | 2014-10-09 |
JP2014527092A5 JP2014527092A5 (ja) | 2015-08-20 |
JP6141269B2 true JP6141269B2 (ja) | 2017-06-07 |
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US (1) | US9249356B2 (ja) |
EP (1) | EP2729551B1 (ja) |
JP (1) | JP6141269B2 (ja) |
CN (1) | CN103732723B (ja) |
WO (1) | WO2013004677A1 (ja) |
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US10344217B2 (en) | 2013-05-24 | 2019-07-09 | Merck Patent Gmbh | Device for controlling the passage of energy, containing a dichroic dye compound |
WO2015090497A1 (de) * | 2013-12-19 | 2015-06-25 | Merck Patent Gmbh | Farbstoff-verbindungen |
WO2016026863A1 (en) | 2014-08-21 | 2016-02-25 | Philips Lighting Holding B.V. | Highly efficient molecules showing resonant energy transfer |
US10364356B2 (en) * | 2014-12-09 | 2019-07-30 | Merck Patent Gmbh | Device for regulating the passage of energy |
DE102015005800A1 (de) | 2015-05-06 | 2016-11-10 | Merck Patent Gmbh | Thiadiazolochinoxalinderivate |
US10868257B2 (en) | 2015-07-10 | 2020-12-15 | Merck Patent Gmbh | Dithioalkylpyrrolopyrroles and the use thereof as dyes |
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US3833287A (en) | 1973-03-08 | 1974-09-03 | Bell Telephone Labor Inc | Guest-host liquid crystal device |
US4378302A (en) * | 1980-12-16 | 1983-03-29 | General Electric Company | Red perylene dichroic dye containing liquid crystal formulations |
JPS6026085A (ja) * | 1983-07-23 | 1985-02-08 | Alps Electric Co Ltd | カラ−液晶表示素子用二色性色素 |
JPS59223786A (ja) * | 1983-06-03 | 1984-12-15 | Alps Electric Co Ltd | カラ−液晶表示素子用二色性色素 |
JPH06318766A (ja) | 1993-03-12 | 1994-11-15 | Toshiba Corp | レーザー発振装置および太陽電池 |
JP3934729B2 (ja) * | 1996-03-29 | 2007-06-20 | 株式会社東芝 | 液晶表示素子 |
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WO2001007533A1 (en) * | 1999-07-26 | 2001-02-01 | New York University | Electron-driven chirality switches |
JP2003201478A (ja) * | 2002-01-10 | 2003-07-18 | Fuji Photo Film Co Ltd | 液晶組成物および液晶素子 |
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DE102005037115A1 (de) | 2005-08-03 | 2007-02-08 | Basf Ag | Mehrfachchromophore |
JP2010520945A (ja) * | 2007-03-13 | 2010-06-17 | テヒニッシェ ウニヴェルシテート アイントホーフェン | インクジェット可能な重合性液晶混合物 |
WO2008110316A1 (en) * | 2007-03-13 | 2008-09-18 | Technische Universitei Eindhoven | Polarization selective scattering security device and method for manufacturing the same |
JP2009046525A (ja) * | 2007-08-13 | 2009-03-05 | Fujifilm Corp | 液晶組成物及び調光材料 |
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