JP7179619B2 - 液晶性材料 - Google Patents
液晶性材料 Download PDFInfo
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- JP7179619B2 JP7179619B2 JP2018560880A JP2018560880A JP7179619B2 JP 7179619 B2 JP7179619 B2 JP 7179619B2 JP 2018560880 A JP2018560880 A JP 2018560880A JP 2018560880 A JP2018560880 A JP 2018560880A JP 7179619 B2 JP7179619 B2 JP 7179619B2
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- 239000007788 liquid Substances 0.000 title claims description 70
- 239000002178 crystalline material Substances 0.000 title claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000000975 dye Substances 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- -1 rylenes Chemical class 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 230000003287 optical effect Effects 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000004056 anthraquinones Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
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- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 2
- 150000002791 naphthoquinones Chemical class 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
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- 239000010410 layer Substances 0.000 description 77
- 239000000203 mixture Substances 0.000 description 14
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- 239000004984 smart glass Substances 0.000 description 10
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- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 4
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- 125000003636 chemical group Chemical group 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
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- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 3
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- 238000001228 spectrum Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- 125000000815 N-oxide group Chemical group 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
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- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
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- 238000013112 stability test Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical class C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
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- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
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- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
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- IGHOZKDBCCFNNC-UHFFFAOYSA-N 1h-imidazole;quinoxaline Chemical compound C1=CNC=N1.N1=CC=NC2=CC=CC=C21 IGHOZKDBCCFNNC-UHFFFAOYSA-N 0.000 description 1
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- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical class C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002478 indolizines Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 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
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000001042 pteridinyl group Chemical class N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000012552 review Methods 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
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- C09K19/586—Optically active dopants; chiral dopants
- C09K19/588—Heterocyclic compounds
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- C09K19/06—Non-steroidal liquid crystal compounds
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- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
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- C09K19/3483—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a non-aromatic ring
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- C09K19/3497—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and nitrogen atoms
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- E06B9/00—Screening or protective devices for wall or similar openings, with or without operating or securing mechanisms; Closures of similar construction
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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
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- 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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- G02F1/1333—Constructional arrangements; Manufacturing methods
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- G02F1/133528—Polarisers
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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
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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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- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
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- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3016—Cy-Ph-Ph
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- C09K19/3001—Cyclohexane rings
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Description
*で印された結合は、前記基と前記化合物の残りの部分とを結合している結合であり、かつ
R1は、それぞれの場合に同一または異なって、Si(R3)3および1個~12個の炭素原子を有するアルキル基であって、F、ClおよびCNから選択される1個以上の基により置換されていてよいアルキル基から選択され、かつ
R2は、それぞれの場合に同一または異なって、H、F、C(=O)R3、CN、Si(R3)3、N(R3)2、P(=O)(R3)2、OR3、S(=O)R3、S(=O)2R3、1個~20個の炭素原子を有する直鎖状のアルキル基またはアルコキシ基、3個~20個の炭素原子を有する分枝鎖状または環状のアルキル基またはアルコキシ基、2個~20個の炭素原子を有するアルケニル基またはアルキニル基、6個~40個の芳香族環原子を有するアリール基、および5個~40個の芳香族環原子を有するヘテロアリール基から選択され、上述のアルキル基、アルコキシ基、アルケニル基、およびアルキニル基、ならびに上述のアリール基およびヘテロアリール基は、それぞれ1個以上の基R3により置換されていてよく、かつ上述のアルキル基、アルコキシ基、アルケニル基、およびアルキニル基中の1個以上のCH2基は、-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SO、またはSO2により置き換えられていてよく、かつ
R3は、それぞれの場合に同一または異なって、H、D、F、CN、1個~20個の炭素原子を有するアルキル基またはアルコキシ基、2個~20個の炭素原子を有するアルケニル基またはアルキニル基、6個~40個の芳香族環原子を有するアリール基、および5個~40個の芳香族環原子を有するヘテロアリール基から選択され、その際、2個以上の基R3は互いに結合されていてよく、かつ環を形成してよく、かつ上述のアルキル基、アルコキシ基、アルケニル基、およびアルキニル基、アリール基およびヘテロアリール基は、FまたはCNで置換されていてよい。
*で印された結合は、前記基と前記化合物の残りの部分とを結合している結合であり、かつ
R1は、前記のように定義され、かつ有利にはメチルである。
Uは、それぞれの場合に同一または異なって、-CH2-、-O-、-S-、および-NH-から選択され、
Spは、2個~10個の炭素原子を有し、それぞれ1個以上の基R4で置換されていてよいアルキレン基、2個~10個の炭素原子を有し、それぞれ1個以上の基R4で置換されていてよいアルケニレン基、2個~10個の炭素原子を有し、それぞれ1個以上の基R4で置換されていてよいアルキニレン基、6個~40個の芳香族環原子を有し、それぞれ1個以上の基R4で置換されていてよいアリール基、および5個~40個の芳香族環原子を有し、それぞれ1個以上の基R4で置換されていてよいヘテロアリール基から選択され、
R1は、前記のように定義され、
R4は、それぞれの場合に同一または異なって、H、D、F、CN、1個~20個の炭素原子を有するアルキル基またはアルコキシ基、2個~20個の炭素原子を有するアルケニル基またはアルキニル基、6個~40個の芳香族環原子を有するアリール基、および5個~40個の芳香族環原子を有するヘテロアリール基から選択され、その際、2個以上の基R3は互いに結合されていてよく、かつ環を形成してよく、かつ上述のアルキル基、アルコキシ基、アルケニル基、およびアルキニル基、アリール基およびヘテロアリール基は、FまたはCNで置換されていてよく、
iは、それぞれの場合に同一または異なって、0または1であり、
pは、2、3、または4である。
存在する変項には、以下のことが当てはまる:
Spは、2個~10個の炭素原子を有し、それぞれ1個以上の基R4で置換されていてよいアルキレン基、2個~10個の炭素原子を有し、それぞれ1個以上の基R4で置換されていてよいアルケニレン基、2個~10個の炭素原子を有し、それぞれ1個以上の基R4で置換されていてよいアルキニレン基、6個~40個の芳香族環原子を有し、それぞれ1個以上の基R4で置換されていてよいアリール基、および5個~40個の芳香族環原子を有し、それぞれ1個以上の基R4で置換されていてよいヘテロアリール基から選択され、
R4は、前記のように定義される。
Cycは、トランス-1,4-シクロヘキシレンを意味し、ここでまた、1個以上の隣接していないCH2基は、-O-および/または-S-により置き換えられていてよく、そしてまた1個以上のH原子はFにより置き換えられていてよく、
Pheは、1,3-フェニレンまたは1,4-フェニレン、有利には1,4-フェニレンを意味し、ここでまた、1個または2個の隣接していないCH基は、Nにより置き換えられていてよく、そしてまた1個以上のH原子はLにより置き換えられていてよく、
Zは、-CH2-、-CF2-、-CO-、-O-、-NH-、-NH-(CO)-、-CH2CH2-、-CH=CH-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、-COO-、-OCO-、-C2F4-、または-CF=CF-を意味し、かつ
Lは、それぞれの場合に同一または異なって、F、Cl、CN、または直鎖状もしくは分枝鎖状の、それぞれ任意にフッ素化された、1個~5個の炭素原子を有するアルキル、アルコキシ、アリールアルキル、またはアルキルアリールアルキルを意味し、ここでまた、1個以上の隣接していないCH2基は、-O-および/または-S-により置き換えられていてよい。
*で印された結合は、前記基と前記化合物の残りの部分とを結合している結合であり、
R21は、それぞれの場合に同一または異なって、H、1個~12個の炭素原子を有するアルキル基および6個~40個の芳香族環原子を有するアリール基から選択される基を有するシリル基、ならびに1個~12個の炭素原子を有するアルキル基であって、F、ClおよびCNから選択される1個以上の基で置換されていてよいアルキル基から選択され、その際、少なくとも1個のR21は、1個~12個の炭素原子を有するアルキル基および6個~40個の芳香族環原子を有するアリール基から選択される基を有するシリル基、ならびに1個~12個の炭素原子を有するアルキル基であって、F、ClおよびCNから選択される1個以上の基で置換されていてよいアルキル基から選択され、
R22は、それぞれの場合に同一または異なって、Hおよび1個~12個の炭素原子を有するアルキル基であって、F、ClおよびCNから選択される1個以上の基により置換されていてよいアルキル基から選択される。
存在する変項には、以下のことが当てはまる:
R21およびR22は、前記のように定義され、
R23は、H、F、Cl、CN、NCS、1個~20個の炭素原子を有するアルキル基、1個~20個の炭素原子を有するアルコキシ基、1個~10個の炭素原子を有するチオアルキル基、2個~20個の炭素原子を有するアルケニル基、および2個~20個の炭素原子を有するアルケニルオキシ基から選択され、ここで、前記アルキル基、アルコキシ基、チオアルキル基、アルケニル基、およびアルケニルオキシ基中の1個以上の水素原子は、F、Cl、またはCNによって置き換えられていてよく、
A21は、それぞれの場合に同一または異なって、
Xは、それぞれの場合に同一または異なって、F、Cl、CN、N3、-NCS、NO2、-C≡C-Rx、1個~12個の炭素原子を有するアルキル基、1個~10個の炭素原子を有するアルコキシ基、および1個~12個の炭素原子を有するチオアルキル基から選択され、ここで、前記アルキル基、アルコキシ基、およびチオアルキル基中の1個以上の水素原子は、F、Cl、またはCNによって置き換えられていてよく、かつ前記アルキル基、アルコキシ基、およびチオアルキル基中の1個以上のCH2基は、OまたはSによって置き換えられていてよく、
Rxは、それぞれの場合に同一または異なって、H、CN、および1個~10個の炭素原子を有するアルキル基から選択され、ここで、前記アルキル基中の1個以上の炭素原子は、F、Cl、またはCNによって置換されていてよく、
Z21は、それぞれの場合に同一または異なって、1個~12個の炭素原子を有するアルキレン基、2個~12個の炭素原子を有するアルケニレン基、2個~12個の炭素原子を有するアルキニレン基、-O-、-S-、-NH-、-(C=O)-O-、-O-(C=O)-、-CF2-O-、-O-CF2-、-O-CH2-、および-CH2-O-から選択され、
kは、それぞれの場合に同一または異なって、0、1、または2であり、
mは、0、1、2、または3であり、
nは、それぞれの場合に同一または異なって、0、1、または2である。
式(II-1)、
式(II-2)、
式(II-3)、
に相当する。
- 導電性の透明な層、有利にはITO製の導電性の透明な層、
- 配向層、
- 本発明による材料を含有するスイッチング層、
- 配向層、
- 導電性の透明な層、有利にはITO製の導電性の透明な層、
- 基板層、有利にはガラスまたはポリマー製の基板層。
- 偏光層、
- 基板層、有利にはガラスまたはポリマー製の基板層、
- 導電性の透明な層、有利にはITO製の導電性の透明な層、
- 配向層、
- 本発明による材料を含有するスイッチング層、
- 配向層、
- 導電性の透明な層、有利にはITO製の導電性の透明な層、
- 基板層、有利にはガラスまたはポリマー製の基板層、
であり、ここで、前記偏光層は、光源の方向に、特に太陽の方向に外側に向けられている。
該セルを、分光学的に測定する(初期値)。次いで、MTS AtlasのサンテストCPS+において70℃のブラックスタンダード温度(=試料の表面温度)に調整し、かつ該試料を気密的に短波長紫外光から遮蔽するSchott社のUVエッジフィルタGG400を使用して16週間にわたり光曝露する。
前記試料を、分光学的に測定し(初期値)、次いで100℃の炉内で7日間にわたり貯蔵する。引き続き、改めてそのスペクトルを室温で測定する。
それぞれのスペクトルの透過曲線から、値x、yおよびzを、M.Richter,Einfuehrung in die Farbmetrik(Sammlung Goeschen,Band 2608)に従って測定する。M.Richter,Einfuehrung in die Farbmetrikに従って、前記値x、yおよびzから、L*、a*、b*を測定し、次いでこれらから相応の差ΔL*、Δa*、およびΔb*を測定する。使用された分光計は、Perkin Elmer Lambda 1050である。
ΔE*=[(ΔL*)2+(Δa*)2+(Δb*)2]0.5
の通りに計算する。
Claims (9)
- 太陽光の通過の調節のための光スイッチング装置であって、色素および式(I)
Uは、それぞれの場合に同一または異なって、-CH2-、-O-、-S-、および-NH-から選択され、
Spは、2個~10個の炭素原子を有し、それぞれ1個以上の基R4で置換されていてよいアルキレン基、2個~10個の炭素原子を有し、それぞれ1個以上の基R4で置換されていてよいアルケニレン基、2個~10個の炭素原子を有し、それぞれ1個以上の基R4で置換されていてよいアルキニレン基、および5個~40個の芳香族環原子を有し、それぞれ1個以上の基R4で置換されていてよいヘテロアリール基から選択され、
R1は、メチル基を意味し、
R4は、それぞれの場合に同一または異なって、H、D、F、CN、1個~20個の炭素原子を有するアルキル基またはアルコキシ基、2個~20個の炭素原子を有するアルケニル基またはアルキニル基、6個~40個の芳香族環原子を有するアリール基、および5個~40個の芳香族環原子を有するヘテロアリール基から選択され、その際、2個以上の基R4は互いに結合されていてよく、かつ環を形成してよく、かつ上述のアルキル基、アルコキシ基、アルケニル基、およびアルキニル基、アリール基およびヘテロアリール基は、FまたはCNで置換されていてよく、
iは、それぞれの場合に同一または異なって、0または1であり、
pは、2、3、または4であり、そして、式(I)の基は、ラジカルであり、その際、酸素原子上の不対電子は1つの点により表示される。)の立体障害された基を有する化合物(I)を含有する液晶性材料の層を含むことを特徴とする、前記光スイッチング装置。 - 前記化合物(I)は、前記液晶性材料中に0.01質量%~1質量%の割合で含まれていることを特徴とする、請求項1記載の光スイッチング装置。
- 前記液晶性材料は、立体障害されたヒドロキシフェニル基を有する化合物(II)、
化合物(II)は、式(2)
*で印された結合は、前記基と前記化合物の残りの部分とを結合している結合であり、
R21は、それぞれの場合に同一または異なって、3個~12個の炭素原子を有する分岐状アルキル基から選択され、F、ClおよびCNから選択される1個以上の基で置換されていてよい、
R22は、それぞれの場合に同一または異なって、Hおよび1個~12個の炭素原子を有するアルキル基であって、F、ClおよびCNから選択される1個以上の基により置換されていてよいアルキル基から選択される、をさらに含有することを特徴とする、請求項1から3までのいずれか1項記載の光スイッチング装置。 - 前記化合物(II)は、前記液晶性材料中に0.01質量%~1質量%の割合で含まれていることを特徴とする、請求項1から4までのいずれか1項記載の光スイッチング装置。
- 前記色素は、二色性色素であることを特徴とする、請求項1から5までのいずれか1項記載の光スイッチング装置。
- 前記液晶性材料は、少なくとも3種の異なる色素を含有することを特徴とする、請求項1から6までのいずれか1項記載の光スイッチング装置。
- 前記色素は、アゾ化合物、アントラキノン、メチン化合物、アゾメチン化合物、メロシアニン化合物、ナフトキノン、テトラジン、リレン、ベンゾチアジアゾール、ピロメテン、およびジケトピロロピロールから選択されることを特徴とする、請求項1から7までのいずれか1項に記載の光スイッチング装置。
- 以下の層順序:
- 偏光層、
- 基板層、
- 導電性の透明な層、
- 配向層、
- 前記液晶性材料を含有するスイッチング層、
- 配向層、
- 導電性の透明な層、
- 基板層、
を有し、ここで、前記偏光層は、太陽の方向に向けられていることを特徴とする、請求項1から8までのいずれか1項に記載の光スイッチング装置。
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