CN109804049B - 液晶介质 - Google Patents
液晶介质 Download PDFInfo
- Publication number
- CN109804049B CN109804049B CN201780062544.2A CN201780062544A CN109804049B CN 109804049 B CN109804049 B CN 109804049B CN 201780062544 A CN201780062544 A CN 201780062544A CN 109804049 B CN109804049 B CN 109804049B
- Authority
- CN
- China
- Prior art keywords
- compounds
- liquid
- atoms
- formulae
- group
- 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.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 239000000975 dye Substances 0.000 claims abstract description 70
- 239000004984 smart glass Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000004429 atom Chemical group 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 7
- 125000006193 alkinyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 3
- 101150065749 Churc1 gene Proteins 0.000 claims description 3
- 102100038239 Protein Churchill Human genes 0.000 claims description 3
- 230000014509 gene expression Effects 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 43
- -1 naphthalene-2, 6-diyl Chemical group 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 13
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 10
- 230000005684 electric field Effects 0.000 description 10
- 239000000126 substance Substances 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000000987 azo dye Substances 0.000 description 6
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 5
- 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 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 210000002858 crystal cell Anatomy 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- OGBWMWKMTUSNKE-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CCCCCC(OC(=O)C(C)=C)OC(=O)C(C)=C OGBWMWKMTUSNKE-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 239000004983 Polymer Dispersed Liquid Crystal Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000004183 alkoxy alkyl 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
- 239000001000 anthraquinone dye Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 2
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[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
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229940097275 indigo Drugs 0.000 description 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical compound C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-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 class 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
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class 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
- 150000004868 1,2,5-thiadiazoles Chemical class 0.000 description 1
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-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
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- GRZJZRHVJAXMRR-UHFFFAOYSA-N 1-cyclohexyl-2-phenylbenzene Chemical group C1CCCCC1C1=CC=CC=C1C1=CC=CC=C1 GRZJZRHVJAXMRR-UHFFFAOYSA-N 0.000 description 1
- RAYZALBEMJMGEA-UHFFFAOYSA-N 1-cyclohexylnaphthalene Chemical compound C1CCCCC1C1=CC=CC2=CC=CC=C12 RAYZALBEMJMGEA-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- OIWIYLWZIIJNHU-UHFFFAOYSA-N 1-sulfanylpyrazole Chemical compound SN1C=CC=N1 OIWIYLWZIIJNHU-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 description 1
- GVQIKUVVJFKEDH-UHFFFAOYSA-N 2,5-dicyclohexyl-5-phenylcyclohexa-1,3-diene Chemical group C1(CCCCC1)C1(CC=C(C=C1)C1CCCCC1)C1=CC=CC=C1 GVQIKUVVJFKEDH-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 1
- YJDDXMSIMBMMGY-UHFFFAOYSA-N 2-cyclohexylpyrimidine Chemical compound C1CCCCC1C1=NC=CC=N1 YJDDXMSIMBMMGY-UHFFFAOYSA-N 0.000 description 1
- YTCKHCHIAZYSEL-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol prop-2-enoic acid 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO.CCCCCC(OC(=O)C=C)OC(=O)C=C YTCKHCHIAZYSEL-UHFFFAOYSA-N 0.000 description 1
- ALGIYXGLGIECNT-UHFFFAOYSA-N 3h-benzo[e]indole Chemical compound C1=CC=C2C(C=CN3)=C3C=CC2=C1 ALGIYXGLGIECNT-UHFFFAOYSA-N 0.000 description 1
- UNTNRNUQVKDIPV-UHFFFAOYSA-N 3h-dithiazole Chemical compound N1SSC=C1 UNTNRNUQVKDIPV-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- IGHSOWSFSFGPAZ-UHFFFAOYSA-N 6-[4-(4-cyanophenyl)phenoxy]hexyl prop-2-enoate Chemical compound C1=CC(OCCCCCCOC(=O)C=C)=CC=C1C1=CC=C(C#N)C=C1 IGHSOWSFSFGPAZ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 101100322581 Caenorhabditis elegans add-1 gene Proteins 0.000 description 1
- 101100322583 Caenorhabditis elegans add-2 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005210 alkyl ammonium group Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- FZICDBOJOMQACG-UHFFFAOYSA-N benzo[h]isoquinoline Chemical compound C1=NC=C2C3=CC=CC=C3C=CC2=C1 FZICDBOJOMQACG-UHFFFAOYSA-N 0.000 description 1
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- DQZKGSRJOUYVPL-UHFFFAOYSA-N cyclohexyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCCCC1 DQZKGSRJOUYVPL-UHFFFAOYSA-N 0.000 description 1
- VJCWGXGMXAVKJU-UHFFFAOYSA-N cyclohexyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1CCCCC1 VJCWGXGMXAVKJU-UHFFFAOYSA-N 0.000 description 1
- 125000005755 decalin-2,6-ylene group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C([H])([*:2])C([H])([H])C([H])([H])C2([H])C([H])([H])C1([H])[*:1] 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- HKNRNTYTYUWGLN-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2C=CS1 HKNRNTYTYUWGLN-UHFFFAOYSA-N 0.000 description 1
- RBBNOVKRLWDEGC-UHFFFAOYSA-M dodecyl-ethyl-dimethylazanium;4-hexoxybenzoate Chemical compound CCCCCCOC1=CC=C(C([O-])=O)C=C1.CCCCCCCCCCCC[N+](C)(C)CC RBBNOVKRLWDEGC-UHFFFAOYSA-M 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003392 indanyl group Chemical class C1(CCC2=CC=CC=C12)* 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
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- FBPVJWUZNQQNEU-UHFFFAOYSA-N n-[2,2-bis(4-chlorophenyl)-2-imidazol-1-ylethyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(N1C=NC=C1)(C=1C=CC(Cl)=CC=1)CNC(=O)C1=CC=CC=C1 FBPVJWUZNQQNEU-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000005053 phenanthridines Chemical class 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 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
- 230000007704 transition Effects 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- 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
- C09K19/60—Pleochroic dyes
-
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
-
- 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
- C09K19/60—Pleochroic dyes
- C09K19/601—Azoic
-
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- 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)
-
- 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
- G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
-
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- 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
-
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/122—Ph-Ph
-
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/123—Ph-Ph-Ph
-
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- 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)
- C09K2019/3009—Cy-Ph
-
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- 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)
- C09K2019/301—Cy-Cy-Ph
-
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- 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
-
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- 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)
- C09K2019/3027—Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene
-
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
- C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
-
- 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
- C09K2219/00—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
- C09K2219/13—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used used in the technical field of thermotropic switches
-
- 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
- G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/13712—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering the liquid crystal having negative dielectric anisotropy
-
- 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
- G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/13725—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on guest-host interaction
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
本发明涉及具有负介电各向异性的液晶介质,由其衍生的宾主型液晶介质以及所述介质在诸如光阀、可切换窗、可切换镜和宾主型显示器的器件中的用途。
液晶特别用作显示器件中的电介质,因为这些物质的光学性质可受到施加电压的影响。基于液晶的电-光器件是本领域技术人员已知的并且可根据各种效果来实现。该类型的器件是,例如具有动态散射的盒,DAP(配向相畸变)盒,具有扭曲向列结构的TN盒,STN(“超扭曲向列”)盒,SBE(“超双折射效应”)盒,OMI(“光学模式干扰”)盒和宾主型盒。
Heilmeier和Zanoni首次描述了上述基于宾主效应的器件(G.H.Heilmeier etal.,Appl.Phys.Lett.,1968,13,91f),并且自此得以广泛应用,其主要用于LC显示元件。在宾主***中,除了液晶之外,LC介质还包含一种或多种二色性染料。由于染料分子吸收的方向依赖性,如果染料与液晶一起改变它们的配向,则可以调节液晶对光的透明度,即LC盒在亮状态与黑暗状态之间的最大对比度取决于二色性染料的配向。当混合在一起时,二色性染料具有使其对向列型液晶分子配向的能力。当向这样的宾主混合物施加电场时,向列型液晶主体分子重新取向并相对于电场配向或垂直于电场,以使它们从电场经历的扭矩最小化。二色性染料(客体)分子不受外部电场的直接影响,但可以使其对液晶主体分子配向。正是它们与液晶分子的相互作用迫使它们重新取向。
特别地,理想的是初始明亮态液晶盒利用负ΔεLC从明亮切换到黑暗,因为在没有施加电压时它们具有透明(明亮)状态,这使得该模式在相对较短的时间内特别适用于通常透明且仅按需调暗的窗户。因此,相较于在必须主动地接通透明状态时消耗能量的模式,该模式更节能。
使用具有负介电各向异性的液晶介质使得液晶盒:
(i)在不存在穿过基板的电场的情况下,液晶和染料分子的长轴相对于基板排列,以使得染料分子不会吸收经引导通过垂直于基板的宾主型液晶混合物的大部分光,无论通过其的光是否偏振,由此液晶盒在不存在电场的情况下保持相对亮的状态,并且
(ii)在存在穿过基板的电场的情况下,液晶和染料分子的长轴相对于基板排列,以使得染料分子吸收经引导通过垂直于基板的宾主型液晶混合物的至少一些光,只要上述的光沿着染料分子的长轴偏振,由此液晶盒在存在电场的情况下变暗。
宾主垂直配向LC显示器描述于,例如,JP2001100253和US357,374。
除了在LC显示器中使用之外,这种类型的器件被已知为切换元件(光阀),用于调节光或能量的通过,例如来自WO2009/141295和WO2010/118422;一个应用的例子是可切换窗口,其可借助电场按需变暗。以及可切换镜,例如,在DE3340670中提出的使用宾主型液晶的用于汽车应用的后视镜。
对于良好的黑暗状态,优选高浓度的染料和低盒间隙。然而,许多染料在现有技术中已知的液晶介质中仅具有有限的溶解度。同时,对于在液晶介质中具有足够溶解度的可用的染料只有有限的选择,并且,同时,适宜于实现高色彩纯度的吸收光谱,理想情况是在电磁波谱的VIS区域具有小的荧光,因为这种发射另外对色彩纯度具有负面影响。在窗户应用中特别不希望有差的色彩纯度,其中出于建筑学原因,美学印象是重要的并且需要尽可能最纯的颜色。为了获得可接受的黑色,必须使用染料的混合物以覆盖电磁光谱的可见部分的整个范围。特别是在灰度切换时,不希望任何偏色。
本发明的一个目的是提供改进的液晶介质,其中二色性染料具有适宜高的溶解度,特别是在应用方面。
为了解决该问题,本发明提供了新型的液晶介质,其中二色性染料惊人地易溶。
本发明涉及包含一种或多种式I化合物的液晶介质,
其中,
R1表示具有至多12个C原子的烷基或烯基,其中一个或多个不相邻的CH2基团可以被-O-和/或具有3-5个碳原子的环烷基环替代,且其中一个或多个H原子可被F替代,
A1在每次出现时相同地或不同地表示:
(a)反式-1,4-亚环己基,其中一个或多个不相邻的CH2基团可被-O-和/或-S-替代,
(b)1,4-亚苯基,其中一个或两个CH基团可被N替代,
(c)反式-1,4-亚环己烯基,
(d)来自下组的基团:1,4-双环[2.2.2]亚辛基,萘-2,6-二基,十氢化萘-2,6-二基和1,2,3,4-四氢化萘-2,6-二基,
其中的基团(a)至(d)可以被一个或两个氟原子取代,
Z1在每次出现时彼此独立地为,
-CO-O-,-O-CO-,-CH2O-,-OCH2-,-CH2CH2-,-CH=CH-,-C≡C-,-(CH2)4-,-OCF2-,-CF2O-,-CF2CF2-或单键,
L11,L12,L13和L14彼此独立地表示H,Cl或F,
n为1,2或3;和
一种或多种选自式IIA,IIB和IIC化合物的化合物,
其中,
R2A,R2B和R2C彼此独立地表示H,具有至多15个C原子的烷基或烯基,其是未取代的,被CN或CF3单取代或被卤素至少单取代,其中,此外,这些基团中的一个或多个CH2基团可以被-O-,-S-,-C≡C-,-CF2O-,-OCF2-,-OC-O-或-O-CO-以使得O原子之间不直接相互连接的方法替代,或表示具有3至6个C原子的环烷基环,
L1-4各自彼此独立地表示F,Cl,CF3或CHF2,
Z2和Z2’各自彼此独立地表示单键,-CH2CH2-,-CH=CH-,-CF2O-,-OCF2-,-CH2O-,-OCH2-,-C(O)O-,-OC(O)-,-C2F4-,-CF=CF-,-CH=CHCH2O-,
p表示1或2,
q表示0或1,和
v表示1-6。
在式IIA和IIB化合物中,Z2可以具有相同或不同的含义。在式IIB化合物中,Z2和Z2’可以具有相同或不同的含义。
在式IIA、IIB和IIC化合物中,R2A,R2B和R2C各自彼此优选地表示具有1-6个C原子的烷基,特别是CH3,C2H5,n-C3H7,n-C4H9,n-C5H11。
在式IIA和IIB化合物中,L1,L2,L3和L4优选地表示L1=L2=F且L3=L4=F,以及,L1=F且L2=Cl,L1=Cl且L2=F,L3=F且L4=CI,L3=Cl和L4=F。在式IIA和IIB中,Z2和Z2’优选各自独立地表示单键,还有-C2H4-或-CH2O-桥。
如果在式IIB中,Z2=-C2H4-或-CH2O-,Z2’优选为单键,或者,如果Z2’=-C2H4-或-CH2O-,则Z2优选地为单键。在式IIA和IIB化合物中,(O)CvH2v+1优选地表示OCvH2v+1,以及CvH2v+1。在式IIC化合物中,(O)CvH2v+1优选地表示CvH2v+1。在式IIC化合物中,L3和L4优选地各自表示F。
卤素表示F,Cl,Br或I。
本发明还涉及液晶介质,其包含一种或多种在可见光波长范围内具有最大吸收的二色性染料。
二色性染料定义为溶解在主体液晶中以吸收光为目的的化合物。在根据本发明的液晶介质中使用的二色性染料的最大吸收没有特别限制,但优选地在黄色区域(Y),品红色区域(M)或青色区域(Y)中具有最大吸收。用于本发明的液晶介质中的二色性染料可以是单一化合物或多种染料的组合。当混合几种染料时,优选使用分别在Y,M和C区具有最大吸收的二色性染料的混合物。二色性染料是本领域技术人员已知的,并且在例如Cowling,Stephen J.,Liquid Crystal Dyes,in Handbook of Liquid Crystals,Wiley-VCHVerlag GmbH&Co.KgaA(2014)中进行了综述。通过混合黄色染料、品红色染料和青色染料显示全色的方法具体描述于“Colour Chemistry”(Sumio Tokita,Maruzen Company,Limited,1982)。黄色区域的范围为430至490nm,品红色区域的范围为500至580nm,以及青色区域的范围为600至700nm。
二色性染料中使用的发色团没有特别限制,但优选地使用偶氮染料、薁类染料、蒽醌染料、苯醌染料、萘醌染料、苯并噻唑染料、二硫苯醌、苝型染料、部花青染料、甲亚胺染料、邻苯二甲酰(phthaloperylene)染料、靛蓝染料、薁类染料、二嗪染料、四嗪染料、聚噻吩染料、萘并咪唑-4,9-二酮染料和吩/>嗪染料。
根据本发明的优选的染料是偶氮染料、苝型染料、蒽醌染料和苯并噻唑染料,特别优选的是偶氮染料。
偶氮染料可含有任何数目的偶氮基团,如单偶氮染料、双偶氮染料、三偶氮染料、四偶氮染料和五偶氮染料,优选地为单偶氮染料、双偶氮染料和三偶氮染料。
偶氮染料中包含的环状结构是芳基和/或杂芳基。
优选的杂芳基是,例如,5-元环,例如吡咯、吡唑、咪唑、1,2,3-***、1,2,4-***、呋喃、噻吩、唑、异/>唑、1,2-噻唑、1,3-噻唑、1,2,3-/>二唑、1,2,4-/>二唑、1,2,5-/>二唑、1,3,4-/>二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、6-元环,如吡啶、哒嗪、嘧啶、吡嗪、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪或缩合基团,如吲哚、苯并咪唑、苯并***、嘌呤、萘并咪唑、菲并咪唑、吡啶咪唑、吡嗪咪唑、喹喔啉咪唑、苯并/>唑、萘并/>唑、蒽并唑、菲并/>唑、异/>唑、苯并噻唑、苯并呋喃、异苯并呋喃、二苯并呋喃、喹啉、异喹啉、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、苯并异喹啉、吖啶、吩噻嗪、吩/>嗪、苯并哒嗪、苯并嘧啶、喹喔啉、吩嗪、萘啶、氮杂咔唑、苯并咔啉、菲啶、菲咯啉、噻吩并[2,3b]噻吩、噻吩并[3,2b]噻吩、二噻吩并噻吩、二氢噻吩并[3,4-b]-1,4-二/>英、异苯并噻吩、二苯并噻吩、苯并噻二氮噻吩或这些基团的组合。
芳基和杂芳基也可以被烷基、环烷基、烷氧基、硫代烷基、烷基氨基、二烷基氨基、氟、氟代烷基或其他芳基或杂芳基取代。
但本发明不限于此,也可以使用已知具有与上述染料相同效果的其他类型的染料。
介质中二色性染料的浓度优选为1重量%或更高,特别优选为1.5重量%或更高,非常特别为2重量%或更高。
优选的式I化合物选自式I-1和I-2化合物:
其中,
R1表示具有至多7个C原子的烷基或烯基,
A11和A12相同或不同地表示
L11和L12彼此独立地表示H或F,和
Z1是-CO-O-,-O-CO-,-CH2O-,-OCH2-,-CH2CH2-,-OCF2-,-CF2O-或单键,优选地为单键。
特别优选的式I化合物选自式I-1至I-8的化合物,非常特别优选式I-1化合物:
优选的式IIA,IIB和IIC化合物如下所示:
其中alkyl和alkyl*各自彼此独立地表示具有1-6个C原子的直链烷基,
alkenyl表示具有2-6个C原子的直链烯基,(O)表示-O-或单键。
根据本发明特别优选的混合物包含一种或多种式IIA-2,IIA-8,IIA-14,IIA-26,IIA-28,IIA-33,IIA-39,IIA-45,IIA-46,IIA-47,IIB-2,IIB-11,IIB-16和IIC-1的化合物。
式IIA和/或IIB化合物在整个混合物中的比例优选为至少20重量%。
根据本发明的特别优选的介质包含至少一种式IIC-1化合物,
其中alkyl和alkyl*具有上述含义,优选的量为>3重量%,特别是>5重量%,特别优选5-30重量%。
根据本发明的混合物的特征在于其中二色性染料的高溶解度。
根据本发明的混合物优选地表现出非常宽的向列相范围,其清亮点≥75℃,优选≥85℃,非常有利的电容阈值,相对高的保持率值,在-20℃和-30℃时同时非常好的低温稳定性,以及低旋转粘度和短响应时间。根据本发明的混合物的特征还在于,除了旋转粘度γ1的改善之外,还可以观察到用于改善响应时间的相对高的弹性常数K33的值。
根据本发明的混合物的一些优选的实施方案如下所示。
优选地,式I化合物基于整个混合物以≥0.5重量%,优选地≥3重量%的量用于液晶介质中。特别优选的液晶介质包含2-20重量%,非常特别优选5-10重量%的式I化合物。
式I化合物优选以20重量%或更低,优选15重量%或更低,特别优选12重量%或更低的量应用于液晶介质中。
根据本发明的液晶介质的优选的实施方案如下所示:
a)液晶介质,其还包含一种或多种式III化合物,
其中
R31和R32各自彼此独立地表示具有至多12个C原子的直链烷基,烯基,烷氧基烷基或烷氧基,和
Z3表示单键、-CH2CH2-、-CH=CH-、-CF2O-、-OCF2-,-CH2O-,-OCH2-,-COO-,-OCO-,-C2F4-,-C4H8-,-CF=CF-。
优选的式III化合物选自下列子式的化合物:
其中alkyl和alkyl*各自彼此独立地表示具有1-6个C原子的直链烷基,并且alkenyl表示具有2-6个C原子的直链烯基。alkenyl优选表示CH2=CH-,CH2=CHCH2CH2-,CH3-CH=CH-,CH3-CH2-CH=CH-,CH3-(CH2)2-CH=CH-,CH3-(CH2)3-CH=CH-或CH3-CH=CH-(CH2)2-。
特别优选的是式III-1和III-3化合物。
式III化合物在整个混合物中的比例优选为至少5重量%。
特别优选的是以下的式III-1的化合物:
特别优选的是以下的式III-3化合物:
b)液晶介质,其还包含一种或多种下式的四环化合物:
其中
R7-10各自彼此独立地具有权利要求2中对于R2A所示的含义之一,和
w和x各自彼此独立地表示1至6。
特别优选的混合物包含至少一种式V-9的化合物。
c)液晶介质,其还包含一种或多种式Y-1至Y-6的化合物,
其中R14-R19各自彼此独立地表示具有1-6个C原子的烷基或烷氧基;z和m各自彼此独立地表示1-6;x表示0,1,2或3。
根据本发明的介质特别优选地包含一种或多种式Y-1至Y-6的化合物,优选地其量为≥5重量%。
d)液晶介质,其还包含一种或多种式T-1至T-21的氟化三联苯,
其中
R表示具有1-7个C原子的直链烷基或烷氧基或具有2-7个C原子的烯基,和
m=0,1,2,3,4,5或6,n表示0,1,2,3或4。
R优选地表示甲基、乙基、丙基、丁基、戊基、己基、甲氧基、乙氧基、丙氧基、丁氧基、戊氧基。
根据本发明的介质优选包含式T-1至T-21的三联苯基,其量为2-30重量%,特别地为5-20重量%。
特别优选的是式T-1,T-2,T-20和T-21的化合物。在这些化合物中,R优选地表示烷基,以及烷氧基,各自具有1-5个C原子。在式T-20的化合物中,R优选地表示烷基或烯基,特别地为烷基。在式T-21的化合物中,R优选地表示烷基。
如果混合物的Δn值近似≥0.1,则三联苯优选地用于根据本发明的混合物中。优选的混合物包含2-20重量%的一种或多种选自化合物T-1至T-21的三联苯化合物。
e)液晶介质还包含一种或多种式B-1至B-4的联二苯基,
其中,
alkyl和alkyl*各自彼此独立地表示具有1-6个C原子的直链烷基,alkenyl和alkenyl*各自彼此独立地表示具有2-6个C原子的直链烯基,并且,alkoxy表示具有1-6个C原子的直链烷氧基。
式B-1至B-4的联二苯在整个混合物中的比例优选为至少3重量%,特别地为≥5重量%。
在式B-1至B-4的化合物中,特别优选地为式B-2的化合物。
特别优选的联二苯是
其中alkyl*表示具有1-6个碳原子的烷基。根据本发明的介质特别优选地包含一种或多种式B-1a和/或B-2c的化合物。
f)液晶介质,包含至少一种式Z-1至Z-7的化合物,
其中
R表示具有1-7个C原子的直链烷基或烷氧基或具有2-7个C原子的烯基,alkyl表示具有1-6个C原子的烷基,和
(O)alkyl表示烷基或O烷基(烷氧基)。
g)液晶介质,包含至少一种式O-1至O-16的化合物,
其中,R1和R2具有R2A表示的含义。R1和R2优选地各自彼此独立地表示具有1-6个C原子的直链烷基或R1表示具有1-6个C原子的直链烷基并且R2表示具有2-6个C原子的烯基。
优选的介质包含一种或多种式O-1,O-3,O-4,O-5,O-9,O-12,O-14,O-15和/或O-16的化合物。
根据本发明的混合物非常特别优选地包含式O-9,O-12和/或O-16的化合物,特别地为5-30%的量。
优选的式O-9的化合物如下所示:
h)液晶介质,包含一种或多种式BA化合物
其中
alkenyl和alkenyl*各自彼此独立地表示具有2-12个C原子的直链烯基,
Z3表示单键,-CH2CH2-,-CH=CH-,-CF2O-,-OCF2-,-CH2O-,-OCH2-,-COO-,-OCO-,-C2F4-,-C4H8-,-CF=CF-。
优选的式BA的化合物如下所示:
i)优选的混合物包含一种或多种式In的二氢化茚化合物,
其中
R11,R12,R13各自彼此独立地表示分别具有1-6个C原子或2-6个C原子的直链烷基、烷氧基、烷氧基烷基或烯基,R12和R13另外表示卤素,优选F,
i表示0,1或2。
优选的式In化合物是下面所示的式In-1至In-16化合物:
特别优选的是式In-1,In-2,In-3和In-4的化合物。
式In和子式In-1至In-16的化合物优选以≥5重量%,特别是5-30重量%,非常特别优选5-25重量%的浓度用于根据本发明的混合物中。
j)该介质还包含一种或多种选自下式的化合物:
在式Q-1至Q-9的化合物中,RQ和XQ各自彼此独立地具有权利要求2中的R2A的含义。RQ和XQ优选表示具有1-6个C原子,特别是具有2-5个C原子的直链烷基。
特别优选的混合物概念如下所示:(所用的首字母缩略词在表1-3和表A中解释。这里n和m各自彼此独立地为1至6的整数)。
根据本发明的混合物优选地包含
-式I的化合物与一种或多种式CPY-n-Om的化合物,特别是CPY-2-O2,CPY-3-O2和/或CPY-5-O2的组合,优选地,基于总混合物的浓度>5%,特别是10-30%,
和/或
-CY-n-Om,优选CY-3-O2,CY-3-O4,CY-5-O2和/或CY-5-O4,优选地,基于总混合物的浓度>5%,特别是15-50%,
和/或
-CCY-n-Om,优选CCY-4-O2,CCY-3-O2,CCY-3-O3,CCY-3-O1和/或CCY-5-O2,优选地,基于总混合物的浓度>5%,特别是10-30%,
此外,根据本发明的优选的混合物,其包含以下混合物概念:
(n和m各自彼此独立地为1到6的整数)
-CPY-n-Om和CY-n-Om,优选地,其基于总混合物的浓度为10-80%,
和/或
-CPY-n-Om和CK-n-F,优选地,其基于总混合物的浓度为10-70%,
和/或
-CPY-n-Om和PY-n-Om,优选地CPY-2-O2和/或CPY-3-O2和PY-3-O2,优选地,其基于总混合物的浓度为10-40%,
和/或
-CBCnm和/或CBC-nmF,其基于总混合物的总浓度为2-10%,
和/或
-PGIY-n-Om,优选地其量为3-15%,
和/或
-PGIGI-n-F,优选地其量为3-15%,
本发明还涉及一种基于宾主效应的包含根据本发明的液晶介质的电光器件,比如光阀、可切换窗、可切换镜、LC显示器、宾主聚合物分散液晶(GHPDLC)膜,宾主聚合物网络液晶(GHPNLC)薄膜,宾主动态散射液晶(GHDSLC)膜。
根据本发明的液晶介质优选具有≤-20℃至≥70℃的向列相,特别优选地为≤-30℃至≥80℃,非常特别优选地为≤-40℃至≥90℃。
这里“具有向列相”的表述在一方面意味着在对应的温度下在低温下没有观察到近晶相和结晶,另一方面,在从向列相加热时仍不会发生清亮。在相应的温度下在流动粘度计中进行低温下的研究,并通过储存在具有对应于电光用途的层厚度的测试盒中至少100小时进行检查。如果在对应的测试盒中在-20℃的温度下的储存稳定性是1000小时或更多,则认为该介质在该温度下是稳定的。在-30℃和-40℃的温度下,相应的时间分别为500小时和250小时。在高温下,通过毛细管中的常规方法测量清亮点。
液晶混合物优选地具有至少60K的向列相范围。
液晶混合物中双折射率Δn的值通常在0.07和0.16之间,优选地在0.08和0.13之间。
根据本发明的液晶混合物的Δε为-0.5至-8.0,特别地为-1.0至-6.0,其中Δε表示介电各向异性。在20℃下的旋转粘度γ1优选≤500mPa·s,特别是≤250mPa·s。
根据本发明的液晶介质具有相对小的阈值电压(V0)的值。它们优选地在1.7V至4.0V的范围内,特别优选地≤3.0V并且非常特别地优选地≤2.7V。
除非另有明确说明,对于本发明,术语“阈值电压”涉及电容阈值(V0),也称为Freedericks阈值。
另外,根据本发明的液晶介质在液晶盒中具有高的电压保持率值。
通常,具有低寻址电压或阈值电压的液晶介质表现出比具有较高寻址电压或阈值电压的液晶介质更低的电压保持率,反之亦然。
对于本发明,术语“介电正性化合物”表示Δε>1.5的化合物,术语“介电中性化合物”表示-1.5≤Δε≤1.5的那些化合物,且术语“介电负性化合物”表示具有Δε<-1.5的那些化合物。这里化合物的介电各向异性的确定是通过将10%的化合物溶解在液晶主体中并确定所得混合物在至少一个测试盒中的电容来进行的,所述测试盒在每种情况下在1kHz下具有垂面配向和沿面配向的20μm的层厚度。测量电压通常为0.5V至1.0V,但总是低于所研究的相应液晶混合物的电容阈值。
本发明所示的所有温度值均以℃来表示。
除一种或多种式I化合物外,所述相还优选地包含4至15,特别地为5至12,特别优选地为<10种的式IIA,IIB和/或IIC化合物。
除了式I化合物和式IIA,IIB和/或IIC化合物之外,还可以存在其他成分,例如以高达总混合物的45%的量存在,但优选高达35%,特别是高达10%。
此外,这些液晶相还可包含多于18种的组分,优选18至25种的组分。
其它成分优选选自向列性或向列型物质,尤其是已知的物质,选自氧化偶氮苯,亚苄基苯胺,联二苯,三联苯,苯基或环己基苯甲酸酯,苯基或环己基环己烷羧酸酯,苯基环己烷,环己基联苯,环己基环己烷,环己基萘,1,4-双环己基联二苯或环己基嘧啶,苯基-或环己基二烷,任选卤代的芪类,苄基苯基醚,二苯乙炔和取代的肉桂酸酯。
适宜作为该类型的液晶相成分的最重要的化合物可用式IV表征,
R20-L-G-E-R21IV
其中L和E各自代表碳环或杂环体系,其来自以下形成的基团:1,4-二取代苯和环己烷环,4,4’-二取代联苯,苯基环己烷和环己基环己烷体系,2,5-二取代嘧啶和1,3-二烷环,2,6-二取代萘,二氢和四氢化萘,喹唑啉和四氢喹唑啉,
G表示
或C-C单键,Q表示卤素优选氯,或-CN,R20和R21各自表示具有最多18个,优选最多8个碳原子的烷基,烯基,烷氧基,烷氧基烷基或烷氧基羰基氧基,或这些基团中之一供选择地表示CN、NC、NO2、NCS、CF3、SF5、OCF3、F、Cl或Br。
在大多数这些化合物中,R20和R21彼此不同,这些基团之一通常是烷基或烷氧基。所举出的取代基的其他变体也是常见的。许多这样的物质或其混合物是可商购的。所有这些物质可以通过文献中已知的方法制备。
对于本领域技术人员来说,不言而喻,根据本发明的液晶还可以包含其中例如H,N,O,Cl和F已被相应的同位素替代的化合物。
可以将非介晶的或介晶的可聚合化合物,后者称为反应性介晶(RM),例如US 6,861,107中公开的,优选非介晶的,进一步加入到根据本发明的混合物中,浓度为基于该混合物,优选10-50重量%,特别优选20-40重量%。可聚合化合物优选选自丙烯酸2-乙基己酯(EHA),丙烯酸1,3,3-三甲基己酯(TMHA),三羟甲基丙烷三丙烯酸酯己二醇二丙烯酸酯(HDDA),己二醇二甲基丙烯酸酯(HDDMA)等,以及甲基丙烯酸甲酯(MMA),丙烯酸乙酯(EA),甲基丙烯酸乙酯(EMA)和6-(4’-氰基联苯-4-基氧基)己基丙烯酸酯(6CBA),和介晶单体。这些混合物还可任选地包含引发剂,例如U.S.6,781,665中所述。引发剂,例如来自BASF的Irganox-1076,优选以0-1%的量加入到包含可聚合化合物的混合物中。这种类型的混合物可用于所谓的宾主型聚合物分散液晶(GHPDLC)。在JP 06-324309 A中描述了GHPDLC显示器。GHPDLC聚合物膜公布于P.Malik,K.K.Raina,Physica B 405(2010)161-166。
对于此,先决条件是液晶混合物本身不包含可聚合组分,其在式M的化合物聚合的条件下同样地聚合。
聚合优选在以下条件下进行:使用规定强度的UV-A灯在规定的时间段内将可聚合组分在盒中聚合,并施加电压(通常为10至30V交流电压,频率范围为60Hz至1kHz)。所用的UV-A光源通常是金属卤化物蒸气灯或强度为50mW/cm2的高压汞灯。这些条件是,例如,含有烯基或链烯氧基侧链的液晶化合物,例如式的化合物不发生聚合,
其中n=2,3,4,5或6。
根据本发明的混合物还可包含常规添加剂,例如稳定剂、抗氧化剂、UV吸收剂、纳米颗粒、微粒等。
在本发明的一个优选的实施方案中,液晶介质包含一种或多种手性掺杂剂。
以下实施例旨在解释本发明而非限制本发明。在上下文中,百分比数据表示重量百分比;所有温度均以摄氏度表示。
在整个专利申请中,1,4-亚环己基环和1,4-苯基环如下所示:
亚环己基环是反式-1,4-亚环己基环。
在整个专利申请和工作实施例中,液晶化合物的结构用首字母缩写词表示。除非另有说明,否则化学式的转化根据表1-3进行。所有基团CnH2n+1,CmH2m+1和Cm'H2m'+1或CnH2n和CmH2m均为直链烷基或亚烷基,在每种情况下,分别具有n,m,m’或z个C原子,n,m,m’和z彼此独立地表示1、2、3、4、5、6、7、8、9、10、11或12,优选1、2、3、4、5或6。表1中编码了各个化合物的环元素,表2中列出了桥连基团,以及表3中指出了化合物的左侧或右侧链的符号的含义。
表1:环元素
表2:桥连基团
表3:侧链
除式IIA化合物和/或IIB和/或IIC以及一种或多种式I化合物外,根据本发明的混合物还优选地包含一种或多种下表A所示的化合物。
表A
使用了以下缩写:
(n,m,m’,z:各自彼此独立地表示1、2、3、4、5或6;
(O)CmH2m+1表示OCmH2m+1或CmH2m+1)
按照本发明可使用的液晶混合物本身以常规的方式制备。通常,以较少量使用的所需量的组分有利地在升高的温度下溶解在构成主要成分的组分中。也可以将组分的溶液混合在有机溶剂中,例如在丙酮、氯仿或甲醇中,并在彻底混合后再次除去溶剂,例如通过蒸馏。
电介质还可以包含本领域技术人员已知的和文献中描述的其他添加剂,例如UV吸收剂、抗氧化剂、纳米颗粒和自由基清除剂。例如,可以添加稳定剂或手性掺杂剂。适用于根据本发明的混合物的稳定剂具体地是表B中列出的那些。
例如,导电盐,优选4-己氧基苯甲酸乙基二甲基十二烷基铵,四苯基硼酸四丁基铵或冠醚的络合盐(参见,例如,Haller等,Mol.Cryst.,Liq.Cryst.,第24卷,第249-258页(1973))以改善导电性,或者可以加入物质以改变向列相的介电各向异性、粘度和/或配向。
例如,在DE-A 22 09 127,22 40 864,23 21 632,23 38 281,24 50 088,26 37430和28 53 728中描述了这种物质。
表B
表B显示了通常添加到根据本发明的混合物中的可能的掺杂剂。该混合物优选包含0-10重量%,特别是0.01-5重量%,特别优选0.01-3重量%的掺杂剂。如果混合物仅包含一种掺杂剂,则其用量为0.01-4重量%,优选0.1-1.0重量%。
表C
例如,可以以0-10%重量的量加入本发明混合物中的稳定剂如下所示。
n=1,2,3,4,5,6或7
n=1,2,3,4,5,6或7
n=1,2,3,4,5,6或7
可用于根据本发明的液晶介质的优选的其它二色性染料的实例列于表D中:
表D
工作实施例:
以下实施例旨在解释本发明而不是限制本发明。在实施例中,m.p.表示熔点,C表示液晶物质的清亮点,单位为摄氏度;沸腾温度b.p.用沸点表示。此外:
C表示结晶固态,S表示近晶相(指数表示相型),N表示向列型,Ch表示胆甾相,I表示各向同性相,Tg表示玻璃化转变温度。两个符号之间的数字表示转换温度,单位为摄氏度。
用于测定式I化合物的光学各向异性Δn的主体混合物是商业混合物ZLI-4792(Merck KGaA)。使用商业混合物ZLI-2857测定介电各向异性Δε。待研究的化合物的物理数据是从加入待研究的化合物后主体混合物的介电常数的变化获得的,并外推至所用化合物的100%。通常,根据溶解度,将10%待研究的化合物溶解在主体混合物中。
除非另有说明,份数或百分数数据表示重量份或重量百分比。
在上下文中,符号和缩写具有以下的含义:
Vo 阈值电压,20℃时的电容[V]
Δn 在20℃和589nm下测量的光学各向异性
Δε 在20℃和1kHz下的介电各向异性
cl.p. 清亮点[℃]
K1 弹性常数,在20℃时“伸展”形变[pN]
K3 弹性常数,在20℃时“弯曲”形变[pN]
γ1 在20℃下测量的旋转粘度[mPa·s],通过磁场中的旋转方法确定
LTS 低温稳定性(向列相),在测试盒中测定。
用于测量阈值电压的显示器具有两个平面平行的外板,其间隔为20μm,并且具有包括SE-1211(Nissan Chemicals)的配向层的电极层位于外板的内侧的顶部,这实现了液晶的垂面配向。
除非另外明确指出,否则本申请中的所有浓度均涉及相应的混合物或混合物组分。所有物理性质均根据“Merck Liquid Crystals,Physical Properties of LiquidCrystals”,1997年11月,Merck KGaA,Germany确定,并且,除非另有明确说明,其适用于20℃的温度。
混合物实施例
对比实施例C1
实施例M1
实施例M2
实施例M3
由混合物C1、M1、M2和M3,制备了具有下表中给出的组成的宾主型液晶混合物GHC1、GH1、GH2、GH3和GH4,使用了由以下组分Dye-1、Dye-2和Dye-3组成的染料混合物,其不同的吸收特性共同产生黑色,并且,在GH3的情况下,包含添加剂Add-1和Add-2。
对比实施例GHC1
实施例GH1
实施例GH2
实施例GH3
实施例GH4
令人惊奇的是,在包含式I化合物PCH-3的混合物M1,M2和M3中,由Dye-1,Dye-2和Dye-3组成的染料混合物显示出相较于在对比实施例C1的混合物中显著更好的溶解性。在对比实施例GHC1的情况下,染料的浓度非常接近饱和极限,这在存储时具有染料在显示面板中结晶的风险。在实施例GH1至GH4的情况下,未达到饱和极限。
宾主型混合物GH1,GH2,GH3和GH4具有非常好的性能,适用于例如光阀、可切换窗户和宾主显示器的器件中的应用,因为它们具有高清亮温度和宽的向列相范围,低阈值电压和非常好的低温稳定性。由于染料Dye-1,Dye-2和Dye-3在混合物M1,M2和M3中的优异溶解性,在施加电压后可以实现具有非常好的黑色(暗)状态的高对比度。
Claims (9)
1.具有负介电各向异性的液晶介质,特征在于其包含一种或多种选自式I-1和I-2的化合物,其在整个混合物中的比例为0.5-20重量%
其中,
R1表示具有至多7个C原子的烷基或烯基,
A11和A12相同或不同地表示
L11和L12彼此独立地表示H或F,和
Z1表示-CO-O-,-O-CO-,-CH2O-,-OCH2-,-CH2CH2-,-OCF2,-CF2O-或单键;
和
一种或多种选自式IIA,IIB和IIC化合物的化合物,
其中,
R2A,R2B和R2C各自彼此独立地表示H,具有最多15个C原子的烷基或烯基,其是未被取代的或被CN或CF3单取代的或被卤素至少单取代的,其中,这些基团中的一个或多个CH2基团可以被-O-,-S-,-C≡C-,-CF2O-,-OCF2-,-OC-O-或-O-CO-以使得O原子不直接相互连接的方式替代,或表示具有3至6个C原子的环烷基环,
L1-4各自彼此独立地表示F,Cl,CF3或CHF2,
Z2和Z2’各自彼此独立地表示单键,-CH2CH2-,-CH=CH-,-CF2O-,-OCF2-,-CH2O-,-OCH2-,-C(O)O-,-OC(O)-,-C2F4-,-CF=CF-,-CH=CHCH2O-,
p表示1或2,
q表示0或1,和
v表示1到6;以及
一种或多种二色性染料,选自下式的化合物:
3.根据权利要求1的液晶介质,其中二色性染料的浓度为1-2重量%。
6.制备根据权利要求1至5中任一项的液晶介质的方法,其特征在于至少将一种或多种选自式I-1和I-2的化合物与一种或多种选自式IIA,IIB和IIC的化合物,一种或多种选自权利要求1限定的二色性染料,和任选的一种或多种添加剂混合以及任选地加入至少一种可聚合化合物。
7.根据权利要求1至5中任一项的液晶介质在光闸、可切换窗、宾主显示器或汽车镜中的用途。
8.电光器件,其特征在于,其含有根据权利要求1至5中任一项所述的液晶介质作为电介质。
9.根据权利要求8所述的器件,其中所述器件是光阀、可切换窗、宾主显示器或可切换镜。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP16194514 | 2016-10-19 | ||
EP16194514.2 | 2016-10-19 | ||
PCT/EP2017/076314 WO2018073160A1 (en) | 2016-10-19 | 2017-10-16 | Liquid-crystalline medium |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109804049A CN109804049A (zh) | 2019-05-24 |
CN109804049B true CN109804049B (zh) | 2023-07-07 |
Family
ID=57153379
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201780062544.2A Active CN109804049B (zh) | 2016-10-19 | 2017-10-16 | 液晶介质 |
Country Status (7)
Country | Link |
---|---|
US (1) | US11466213B2 (zh) |
EP (1) | EP3529334B1 (zh) |
JP (1) | JP7100027B2 (zh) |
KR (1) | KR102487931B1 (zh) |
CN (1) | CN109804049B (zh) |
TW (1) | TWI751207B (zh) |
WO (1) | WO2018073160A1 (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP7186553B2 (ja) | 2018-08-31 | 2022-12-09 | 株式会社Lixil | 流し台用の被覆部材、被覆構造、施工方法 |
WO2020152206A1 (en) * | 2019-01-25 | 2020-07-30 | Merck Patent Gmbh | Liquid-crystalline medium |
CN114410313A (zh) * | 2022-01-18 | 2022-04-29 | 苏州汉朗光电有限公司 | 一种液晶组合物和宽温高对比度的液晶调光装置 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5328637A (en) * | 1991-02-25 | 1994-07-12 | Hoffmann-La Roche Inc. | Alkinyl-derivatives and their use in liquid crystalline mixtures |
TW589362B (en) * | 1998-06-02 | 2004-06-01 | Chisso Corp | Alkenyl compound having a negative delta epsilon value, liquid crystal composition, and liquid crystal display device |
WO2010057575A1 (de) * | 2008-11-19 | 2010-05-27 | Merck Patent Gmbh | Flüssigkristallines medium |
CN102892862A (zh) * | 2010-05-19 | 2013-01-23 | 默克专利股份有限公司 | 包含液晶介质的光开关元件 |
CN104321410A (zh) * | 2012-05-25 | 2015-01-28 | 默克专利股份有限公司 | 介晶介质和液晶显示器 |
CN104496767A (zh) * | 2014-12-30 | 2015-04-08 | 石家庄诚志永华显示材料有限公司 | 醚类液晶化合物及其制备方法与应用 |
CN105229117A (zh) * | 2013-05-14 | 2016-01-06 | 默克专利股份有限公司 | 液晶介质和液晶器件 |
CN105348849A (zh) * | 2015-10-10 | 2016-02-24 | 烟台显华化工科技有限公司 | 一种偶氮型染料及染料液晶组合物 |
CN107949621A (zh) * | 2015-09-08 | 2018-04-20 | 默克专利股份有限公司 | 光调制元件 |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US357374A (en) | 1887-02-08 | Ors of one-third to gardner p | ||
BE795849A (fr) | 1972-02-26 | 1973-08-23 | Merck Patent Gmbh | Phases nematiques modifiees |
US3814700A (en) | 1972-08-03 | 1974-06-04 | Ibm | Method for controllably varying the electrical properties of nematic liquids and dopants therefor |
DE2450088A1 (de) | 1974-10-22 | 1976-04-29 | Merck Patent Gmbh | Biphenylester |
DE2637430A1 (de) | 1976-08-20 | 1978-02-23 | Merck Patent Gmbh | Fluessigkristallines dielektrikum |
DE2853728A1 (de) | 1978-12-13 | 1980-07-17 | Merck Patent Gmbh | Fluessigkristalline carbonsaeureester, verfahren zu ihrer herstellung, diese enthaltende dielektrika und elektrooptisches anzeigeelement |
US4514045A (en) * | 1981-06-22 | 1985-04-30 | Minnesota Mining And Manufacturing Company | Helichromic-smectic liquid crystal compositions and display cells |
DE3340670A1 (de) | 1983-11-10 | 1985-05-23 | Licentia Patent-Verwaltungs-Gmbh, 6000 Frankfurt | Elektronisch schaltbarer spiegel |
JPH0759702B2 (ja) * | 1987-09-07 | 1995-06-28 | 三菱電機株式会社 | ゲスト・ホスト液晶組成物 |
JPH06324309A (ja) | 1993-02-19 | 1994-11-25 | Hitachi Cable Ltd | ポリマー分散型液晶表示素子 |
JP2001100253A (ja) | 1999-09-27 | 2001-04-13 | Kyocera Corp | 液晶表示装置 |
CN1204445C (zh) | 2002-02-04 | 2005-06-01 | 富士通显示技术株式会社 | 液晶显示装置及其制造方法 |
DE50306559D1 (de) | 2002-07-06 | 2007-04-05 | Merck Patent Gmbh | Flüssigkristallines Medium |
JP2008248165A (ja) | 2007-03-30 | 2008-10-16 | Optrex Corp | ゲストホスト液晶組成物および液晶表示パネル |
US8927856B2 (en) | 2008-05-21 | 2015-01-06 | Peer+B.V. | Optical device with anisotropic luminescent material |
US8623476B2 (en) * | 2008-11-28 | 2014-01-07 | Fujifilm Corporation | Polarizing element and method of producing the same |
US8284336B2 (en) | 2009-04-10 | 2012-10-09 | Ravenbrick Llc | Thermally switched optical filter incorporating a guest-host architecture |
WO2014090367A1 (en) | 2012-12-13 | 2014-06-19 | Merck Patent Gmbh | Liquid-crystalline medium |
WO2014135240A2 (de) * | 2013-03-05 | 2014-09-12 | Merck Patent Gmbh | Vorrichtung zur regulierung des energie-durchtritts |
WO2016072498A1 (ja) | 2014-11-07 | 2016-05-12 | 日産化学工業株式会社 | 液晶表示素子 |
-
2017
- 2017-10-16 EP EP17781146.0A patent/EP3529334B1/en active Active
- 2017-10-16 KR KR1020197014220A patent/KR102487931B1/ko active IP Right Grant
- 2017-10-16 US US16/343,147 patent/US11466213B2/en active Active
- 2017-10-16 WO PCT/EP2017/076314 patent/WO2018073160A1/en unknown
- 2017-10-16 CN CN201780062544.2A patent/CN109804049B/zh active Active
- 2017-10-16 JP JP2019520608A patent/JP7100027B2/ja active Active
- 2017-10-18 TW TW106135597A patent/TWI751207B/zh active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5328637A (en) * | 1991-02-25 | 1994-07-12 | Hoffmann-La Roche Inc. | Alkinyl-derivatives and their use in liquid crystalline mixtures |
TW589362B (en) * | 1998-06-02 | 2004-06-01 | Chisso Corp | Alkenyl compound having a negative delta epsilon value, liquid crystal composition, and liquid crystal display device |
WO2010057575A1 (de) * | 2008-11-19 | 2010-05-27 | Merck Patent Gmbh | Flüssigkristallines medium |
CN102892862A (zh) * | 2010-05-19 | 2013-01-23 | 默克专利股份有限公司 | 包含液晶介质的光开关元件 |
CN104321410A (zh) * | 2012-05-25 | 2015-01-28 | 默克专利股份有限公司 | 介晶介质和液晶显示器 |
CN105229117A (zh) * | 2013-05-14 | 2016-01-06 | 默克专利股份有限公司 | 液晶介质和液晶器件 |
CN104496767A (zh) * | 2014-12-30 | 2015-04-08 | 石家庄诚志永华显示材料有限公司 | 醚类液晶化合物及其制备方法与应用 |
CN107949621A (zh) * | 2015-09-08 | 2018-04-20 | 默克专利股份有限公司 | 光调制元件 |
CN105348849A (zh) * | 2015-10-10 | 2016-02-24 | 烟台显华化工科技有限公司 | 一种偶氮型染料及染料液晶组合物 |
Non-Patent Citations (1)
Title |
---|
宾主型液晶彩色负性显示的研究;施善定等;《华东理工大学学报》;19850630(第03期);第389-396页 * |
Also Published As
Publication number | Publication date |
---|---|
EP3529334B1 (en) | 2020-10-07 |
US11466213B2 (en) | 2022-10-11 |
US20190316037A1 (en) | 2019-10-17 |
WO2018073160A1 (en) | 2018-04-26 |
JP7100027B2 (ja) | 2022-07-12 |
EP3529334A1 (en) | 2019-08-28 |
CN109804049A (zh) | 2019-05-24 |
JP2019533052A (ja) | 2019-11-14 |
TWI751207B (zh) | 2022-01-01 |
KR20190069513A (ko) | 2019-06-19 |
TW201816094A (zh) | 2018-05-01 |
KR102487931B1 (ko) | 2023-01-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6775916B2 (ja) | 液晶媒体 | |
KR101547359B1 (ko) | 액정 매질 | |
TWI437079B (zh) | 液晶介質 | |
JP2020189989A (ja) | 液晶媒体 | |
KR20110005272A (ko) | 액정 매질 | |
CN110628441A (zh) | 液晶介质 | |
CN109804049B (zh) | 液晶介质 | |
KR20080057175A (ko) | 액정 매질 | |
JP6973996B2 (ja) | 液晶媒体 | |
WO2021233797A1 (en) | Liquid-crystalline medium | |
TWI668300B (zh) | 液晶介質 | |
TWI766966B (zh) | 液晶介質 | |
CN111492037A (zh) | 液晶介质 | |
KR20210116635A (ko) | 액정 매질 | |
CN111433324A (zh) | 液晶介质 | |
KR20160146555A (ko) | 액정 매질 | |
TW202018065A (zh) | 液晶介質 | |
TWI845599B (zh) | 液晶介質 | |
JP7086914B2 (ja) | 液晶媒体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |