JP7447099B2 - アゾ色素 - Google Patents
アゾ色素 Download PDFInfo
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- JP7447099B2 JP7447099B2 JP2021516791A JP2021516791A JP7447099B2 JP 7447099 B2 JP7447099 B2 JP 7447099B2 JP 2021516791 A JP2021516791 A JP 2021516791A JP 2021516791 A JP2021516791 A JP 2021516791A JP 7447099 B2 JP7447099 B2 JP 7447099B2
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- 239000000987 azo dye Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 231
- 125000000217 alkyl group Chemical group 0.000 claims description 122
- 125000004432 carbon atom Chemical group C* 0.000 claims description 118
- -1 thiazole-2,5-diyl Chemical group 0.000 claims description 70
- 239000000975 dye Substances 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 53
- 125000003342 alkenyl group Chemical group 0.000 claims description 48
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 229910052731 fluorine Inorganic materials 0.000 claims description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 32
- 239000004973 liquid crystal related substance Substances 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 239000000049 pigment Substances 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 238000004040 coloring Methods 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004958 1,4-naphthylene group Chemical group 0.000 claims description 3
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 2
- 239000004065 semiconductor Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 description 21
- 229920000728 polyester Polymers 0.000 description 20
- 230000009102 absorption Effects 0.000 description 18
- 238000010521 absorption reaction Methods 0.000 description 18
- 125000001072 heteroaryl group Chemical group 0.000 description 16
- 230000001276 controlling effect Effects 0.000 description 12
- 239000011521 glass Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 101150065749 Churc1 gene Proteins 0.000 description 9
- 102100038239 Protein Churchill Human genes 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000010408 film Substances 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 230000010287 polarization Effects 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 230000008033 biological extinction Effects 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- DHWADSHFLSDMBJ-UHFFFAOYSA-N 4,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,1,3-benzothiadiazole Chemical compound O1C(C)(C)C(C)(C)OB1C(C1=NSN=C11)=CC=C1B1OC(C)(C)C(C)(C)O1 DHWADSHFLSDMBJ-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 229910000071 diazene Inorganic materials 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 239000007850 fluorescent dye Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 238000000819 phase cycle Methods 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 5
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 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 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 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 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229930192627 Naphthoquinone Natural products 0.000 description 3
- 101000794096 Papio anubis Theta defensin subunit A Proteins 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 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 3
- 150000002791 naphthoquinones Chemical class 0.000 description 3
- 150000002979 perylenes Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- QFBLQWBOVYEGRD-UHFFFAOYSA-N (4-bromophenyl)-[4-(2-ethylhexoxy)naphthalen-1-yl]diazene Chemical compound BrC1=CC=C(C=C1)N=NC1=CC=C(C2=CC=CC=C12)OCC(CCCC)CC QFBLQWBOVYEGRD-UHFFFAOYSA-N 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-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
- BMANTKYMUCXCIM-UHFFFAOYSA-N 2-bromo-5-[4-(3-ethylheptyl)-2-fluorophenyl]thiophene Chemical compound BrC=1SC(=CC=1)C1=C(C=C(C=C1)CCC(CCCC)CC)F BMANTKYMUCXCIM-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group 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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920004933 Terylene® Polymers 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 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
- 125000005248 alkyl aryloxy group Chemical group 0.000 description 2
- 125000005196 alkyl carbonyloxy 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
- 229910052785 arsenic Inorganic materials 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 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 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 238000004737 colorimetric analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical group C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical group C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 230000005670 electromagnetic radiation Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical group C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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 Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910052714 tellurium Inorganic materials 0.000 description 2
- 150000001911 terphenyls Chemical class 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- IUBJRXSUFQTSSL-UHFFFAOYSA-N (4-bromophenyl)-(4-propylphenyl)diazene Chemical compound BrC1=CC=C(C=C1)N=NC1=CC=C(C=C1)CCC IUBJRXSUFQTSSL-UHFFFAOYSA-N 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical group C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical group 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 group C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical group C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical group C=1C=NSN=1 UDGKZGLPXCRRAM-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
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- 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
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- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
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- C07D513/04—Ortho-condensed systems
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- Plural Heterocyclic Compounds (AREA)
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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Description
W11、W12は同一または異なって、O、SまたはSeを表し、
Rzは、それぞれの出現で同一または異なって、H、ハロゲン、1~25個のC原子を有する直鎖状、分岐状または環状のアルキルを表し、該基において加えてOおよび/またはS原子が互いに直接連結されないようにして、1個以上の隣接しないCH2基は、-O-、-S-、-CO-、-CO-O-、-O-CO-または-O-CO-O-で置き換えられてよく、および該基において加えて、1個以上のH原子は、FまたはClで置き換えられてよく、
A11、A12は、それぞれ互いに独立に、アリールまたはヘテロアリール基を表し、該基は、1個以上の基Lで置換されてよく、
A21、A22は、それぞれ互いに独立に、A11の通り定義されるか、または3~10個のC原子を有する環状アルキル基を表し、該基において1~4個の隣接しないCH2基は、2個のO原子が隣接しないようにして、Oで置き換えられてよく、
Lは、それぞれの出現で同一または異なって、OH、CH2OH、F、Cl、Br、I、-CN、-NO2、SF5、-NCO、-NCS、-OCN、-SCN、-C(=O)N(Rz)2、-C(=O)Rz、-N(Rz)2、置換されてよいシリル、6~20個のC原子を有する置換されてよいアリール、または1~25個のC原子を有する直鎖状もしくは分岐状のアルキル、アルコキシ、アルキルカルボニル、アルコキシカルボニル、アルキルカルボニルオキシまたはアルコキシカルボニルオキシ(該基において加えて、1個以上のH原子は、FまたはClで置き換えられてよい。)、アリールまたはヘテロアリール基(該基は、1個以上の基Lで置換されてよい。)を表し、あるいは、また2個の隣接する基Lは共に、2~10個C原子を有する直鎖状または分岐状のアルキレン基(該基において、1個、数個または全てのH原子は、Fで置き換えられてよく、該基において1個以上の-CH2CH2-基は、-CH=CH-で置き換えられ得る。)を表し、
Z10、Z11、Z12は、それぞれの出現で同一または異なって、単結合、-N=N-、-CH=N-、-N=CH-、-N=N(O)-、-N(O)=N-、-CRx1=CRx2-、-(CRx1=CRx2)2-、-C≡C-、-C(=O)-、-CH=CH-C(=O)-、-C(=O)-CH=CH-、-CH=CH-COOまたは-OCO-CH=CH-を表し、
Z21、Z22は、それぞれの出現で同一または異なってZ10の意味の1つを有するか、または-O-、-S-、-CRy1Ry2-、-CF2O-、-OCF2-、-C(O)-O-、-O-C(O)-、-O-C(O)-O-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2S-、-SCF2-、-(CH2)n1-、-CF2CH2-、-CH2CF2-または-(CF2)n1-を表し、
Rx1、Rx2は互いに独立に、H、F、Cl、CNまたは1~12個のC原子を有するアルキルを表し、
Ry1、Ry2は、それぞれ互いに独立に、Hまたは1~12個のC原子を有するアルキルを表し、
Rx11、Rx12、Rx13、Rx14は互いに独立に、H、F、Cl、CNまたは1~12個のC原子を有するアルキル、アルケニル、アルコキシまたはアルケニルオキシを表し、
rおよびtは互いに独立に、0、1または2、好ましくは0または1を表し、
sは0または1、好ましくは0であり、および
n1は、1、2、3または4を表し、
ただしZ10、Z11、Z12、Z21、Z22の1個以上、好ましくは1個、2個または3個は-N=N-を表す。
式Iの1種類以上の化合物および任意の更なる二色性色素を含む色素成分A)と、
1種類以上、好ましくは2種類以上のメソゲン化合物を含み、下で「LCホスト混合物」とも呼ばれる液晶成分B)と
を含むLC媒体に関する。
インドール、イソインドール、インドリジン、インダゾール、ベンズイミダゾール、ベンゾトリアゾール、プリン、ナフトミダゾール、フェナントイミダゾール、ピリジミダゾール、ピラジンイミダゾール、キノキサリンイミダゾール、ベンゾオキサゾール、ナフトオキサゾール、アントオキサゾール、フェナントオキサゾール、イソオキサゾール、ベンゾチアゾール、ベンゾフラン、イソベンゾフラン、ジベンゾフラン、キノリン、イソキノリン、プテリジン、ベンゾ-5,6-キノリン、ベンゾ-6,7-キノリン、ベンゾ-7,8-キノリン、ベンゾイソキノリン、アクリジン、フェノチアジン、フェノキサジン、ベンゾピリダジン、ベンゾピリミジン、キノキサリン、フェナジン、ナフチリジン、アザカルバゾール、ベンゾカルボリン、フェナントリジン、フェナントロリン、チエノ[2,3b]チオフェン、チエノ[3,2b]チオフェン、ジチエノチオフェン、ジヒドロチエノ[3,4-b]-1,4-ジオキシン、イソベンゾチオフェン、ジベンゾチオフェン、ベンゾチアジアゾチオフェンなどの縮合基、または、これらの基の組み合わせである。また、ヘテロアリール基は、アルキル、アルコキシ、チオアルキル、フッ素、フルオロアルキル、または1個の更なるアリールまたはヘテロアリール基で置換されてよい。
Z11、Z12、Z22は、それぞれの出現で同一または異なって単結合、-CRx1=CRx2-または-C≡C-、特に好ましくは単結合を表し、
R11およびR12は互いに独立に、1~15個のC原子を有する直鎖状のアルキルもしくはアルコキシ基または3~25個のC原子を有する分岐状のアルキルもしくはアルコキシ基、特に好ましくはn-ペンチル、n-ヘキシル、n-ヘプチルまたは2-エチルヘキシル、2-エチルヘプチル、2-エチルオクチル、2-エチルノニル、2-エチルデシル、3-エチルヘキシル、3-エチルヘプチル、3-エチルオクチル、3-エチルノニル、3-エチルデシル、2-オクチルドデシルを表し、
A11、A12は、1,4-フェニレン、1,4-ナフチレン、2,6-ナフチレン、チアゾール-2,5-ジイル、チオフェン-2,5-ジイルまたはチエノチオフェン-2,5-ジイルを表す。該基は上で定義される1個以上の基L、特にF、Cl、それぞれ1~5個のC原子を有する分岐状もしくは分岐していないアルキル、アルケニルもしくはアルコキシ、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシルまたはOHで置換されてよく、
Rx11、Rx12、Rx13、Rx14は互いに独立に、H、F、Cl、CN、それぞれ1~12個のC原子を有するアルキル、アルケニル、アルコキシまたはアルケニルオキシ、好ましくはHまたは1~6個のC原子を有するアルキルを表す。
R11およびR12は互いに独立に、1~15個のC原子を有する直鎖状のアルキルもしくはアルコキシ基または3~25個のC原子を有する分岐状のアルキルもしくはアルコキシ基、特に好ましくはn-ペンチル、n-ヘキシル、n-ヘプチルまたは2-エチルヘキシル、2-エチルヘプチル、2-エチルオクチル、2-エチルノニル、2-エチルデシル、3-エチルヘキシル、3-エチルヘプチル、3-エチルオクチル、3-エチルノニル、3-エチルデシルまたは2-オクチルドデシルを表す。
Zx、Zy、ZACは、それぞれ互いに独立に、-CH2CH2-、-CH=CH-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、-CO-O-、-O-CO-、-C2F4-、-CF=CF-、-CH=CH-CH2O-または単結合、好ましくは単結合を表し、および
L1~4は、それぞれ互いに独立に、F、Cl、CN、OCF3、CF3、CH3、CH2F、CHF2を表す。
Zyは、-CH2CH2-、-CH=CH-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、-CO-O-、-O-CO-、-C2F4-、-CF=CF-、-CH=CH-CH2O-または単結合、好ましくは単結合を表す。
R5およびR6は、それぞれ互いに独立に、1~12個のC原子を有するアルキル(該基において加えてO原子が互いに直接連結されないようにして、1個または2個の隣接しないCH2基は、-O-、-CH=CH-、-CO-、-OCO-または-COO-で置き換えられてよい。)、好ましくは1~6個のC原子を有するアルキルまたはアルコキシを表し、
fは、1または2を表し、
R1およびR2は、それぞれ互いに独立に、1~12個のC原子を有するアルキルを表し、該基において加えてO原子が互いに直接連結されないようにして、1個または2個の隣接しないCH2基は、-O-、-CH=CH-、-CO-、-OCO-または-COO-で置き換えられてよく、
Zyは、-CH2CH2-、-CH=CH-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、-CO-O-、-O-CO-、-C2F4-、-CF=CF-、-CH=CH-CH2O-または単結合、好ましくは単結合を表し、
L1およびL2は、それぞれ互いに独立に、F、Cl、OCF3、CF3、CH3、CH2F、CHF2を表す。
ZO1は、-CH2CH2-、-CF2CF2-、-C=C-または単結合を表し、
ZO2は、CH2O、-C(O)O-、-CH2CH2-、-CF2CF2-または単結合を表し、
oは、1またh2である。
R10およびR11は、それぞれ互いに独立に、1~12個のC原子を有するアルキル(該基において加えてO原子が互いに直接連結されないようにして、1個または2個の隣接しないCH2基は、-O-、-CH=CH-、-CO-、-OCO-または-COO-で置き換えられてよい。)、好ましくは1~6のC原子を有するアルキルまたはアルコキシを表し、
およびR10およびR11は好ましくは、1~6個のC原子を有する直鎖状のアルキルもしくはアルコキシまたは2~6個のC原子を有する直鎖状のアルキレンを表し、
Z1およびZ2は、それぞれ互いに独立に、-C2H4-、-CH=CH-、-(CH2)4-、-(CH2)3O-、-O(CH2)3-、-CH=CH-CH2CH2-、-CH2CH2CH=CH-、-CH2O-、-OCH2-、-CO-O-、-O-CO-、-C2F4-、-CF=CF-、-CF=CH-、-CH=CF-、-CH2-または単結合を表す。
R11およびR12は、それぞれ互いに独立に上でR11に示される意味の1つを有し、
環Mは、trans-1,4-シクロヘキシレンまたは1,4-フェニレンであり、
Zmは、-C2H4-、-CH2O-、-OCH2-、-CO-O-または-O-CO-であり、
cは、0、1または2であり、
好ましくは3~20重量%の量、特に3~15重量%の量である。
R1およびR2は、それぞれ互いに独立に、1~12個のC原子を有するアルキル(該基において加えてO原子が互いに直接連結されないようにして、1個または2個の隣接しないCH2基は、-O-、-CH=CH-、-CO-、-OCO-または-COO-で置き換えられてよい。)、好ましくは1~6のC原子を有するアルキルまたはアルコキシを表し、
L1およびL2は、それぞれ互いに独立に、F、Cl、OCF3、CF3、CH3、CH2F、CHF2を表す。
R20は、それぞれ同一または異なって、1~15個のC原子を有するハロゲン化もしくは無置換のアルキルまたはアルコキシ基を表し、ただし加えて、これらの基においてO原子が互いに直接連結されないようにして、1個以上のCH2基は、それぞれ互いに独立に、-C≡C-、-CF2O-、-CH=CH-、
X20は、それぞれ同一または異なって、F、Cl、CN、SF5、SCN、NCS、それぞれ6個までのC原子を有するハロゲン化されたアルキル基、ハロゲン化されたアルケニル基、ハロゲン化されたアルコキシ基またはハロゲン化されたアルケニルオキシ基を表し、
Y20~24は、それぞれ同一または異なって、HまたはFを表し、
R20、X20およびY20~23は、上で示される意味を有し、および
Z20は、-C2H4-、-(CH2)4-、-CH=CH-、-CF=CF-、-C2F4-、-CH2CF2-、-CF2CH2-、-CH2O-、-OCH2-、-COO-または-OCF2-、また式VおよびVIにおいては単結合も、また式VおよびVIIIにおいては-CF2O-も表し、
rは、0または1を表し、および
sは、0または1を表す。
Lは、HまたはFを表し、
「alkenyl」は、C2~6アルケニルを表す。
好ましくはデバイスは、建物、容器、車両または他の実質的に閉鎖された空間内に、上記の通り比較的高いエネルギー透過率を有する開口に収容される。デバイスは、特に環境との空気の交換が限られており、光エネルギーの形態で外部からのエネルギーの入力が可能な光透過境界面を有するのであれば、一般に任意で所望の内部空間のために使用できる。光透過領域、例えば窓領域を介して強い日射を受ける内部空間用のためにデバイスを使用することは特に関連性がある。
・基板層、好ましくはガラスまたはポリマーを含む
・導電性層、好ましくはITOを含む
・配向層
・式Iの1種類以上の化合物を含むスイッチ層
・配向層
・導電性層、好ましくはITOを含む
・基板層、好ましくはガラスまたはポリマーを含む。
表Eは、本発明によるLC媒体に添加し得る可能性のある安定剤を示す。
(ここでnは1~12の整数、好ましくは1、2、3、4、5、6、7または8を表し、末端メチル基は示されていない)。
R=[E(p)-E(s)]/[E(p)+2×E(s)]
調製された色素はエネルギーの通過を制御するためのデバイスにおける使用のためのそれらの適合性を確立するために、それらの物理的性質に関して検討される。比較のために、BTD-1~BTD-3およびAD-1~AD-3の状態で知られている化合物の対応する特性が与えられる。
ネマチックLCホスト混合物N-1~N-20を、以下の通り調製する。
Claims (16)
- 式I-1~I-4の化合物から成る群より選択される1種類以上の化合物および任意の更なる二色性色素を含む色素成分A)と、および
1種類以上のメソゲン化合物を含み、「LCホスト混合物」とも呼ばれる液晶成分B)と
を含むことを特徴とする、LC媒体。
Z 11 、Z 12 およびZ 22 は、単結合を表し、
R 11 およびR 12 は互いに独立に、1~15個のC原子を有する直鎖状のアルキルもしくはアルコキシ基または3~25個のC原子を有する分岐状のアルキルもしくはアルコキシ基を表し、
A 11 、A 12 は、1,4-フェニレン、1,4-ナフチレン、2,6-ナフチレン、チアゾール-2,5-ジイル、チオフェン-2,5-ジイルまたはチエノチオフェン-2,5-ジイルを表し、該基はF、Cl、それぞれ1~5個のC原子を有する分岐状もしくは分岐していないアルキル、アルケニルもしくはアルコキシ、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシルまたはOHで置換されてよく、
式中、
R x11 、R x12 、R x13 、R x14 は、互いに独立にHまたは1~6個のC原子を有するアルキルを表す。) - R11およびR12は互いに独立に3~25個のC原子を有する分岐状のアルキル基を表し、ただし1個以上のH原子はFで置き換えられ得て、1個以上のCH2基はOおよび/またはNHで置き換えられ得て、1個以上のCH基はNで置き換えられ得る、請求項1または2に記載のLC媒体。
- 式I-1~I-4の化合物。
Z 11 、Z 12 およびZ 22 は、単結合を表し、
R 11 およびR 12 は互いに独立に、1~15個のC原子を有する直鎖状のアルキルもしくはアルコキシ基または3~25個のC原子を有する分岐状のアルキルもしくはアルコキシ基を表し、
A 11 、A 12 は、1,4-フェニレン、1,4-ナフチレン、2,6-ナフチレン、チアゾール-2,5-ジイル、チオフェン-2,5-ジイルまたはチエノチオフェン-2,5-ジイルを表し、該基はF、Cl、それぞれ1~5個のC原子を有する分岐状もしくは分岐していないアルキル、アルケニルもしくはアルコキシ、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシルまたはOHで置換されてよく、
式中、
R x11 、R x12 、R x13 、R x14 は、互いに独立にHまたは1~6個のC原子を有するアルキルを表す。) - R11およびR12は互いに独立に3~25個のC原子を有する分岐状のアルキル基を表し、ただし1個以上のH原子はFで置き換えられ得て、1個以上のCH2基はOおよび/またはNHで置き換えられ得て、1個以上のCH基はNで置き換えられ得る、請求項5または6に記載の化合物。
- 媒体は、負の誘電異方性を有し、式CY、PYおよびACの化合物の群から選択される1種類以上の化合物を含むLCホスト混合物を含む、請求項1~4のいずれか1項に記載のLC媒体。
Zx、Zy、ZACは、それぞれ互いに独立に、-CH2CH2-、-CH=CH-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、-CO-O-、-O-CO-、-C2F4-、-CF=CF-、-CH=CH-CH2O-または単結合を表し、
L1~4は、それぞれ互いに独立にF、Cl、CN、OCF3、CF3、CH3、CH2F、CHF2を表し、
aは、1または2であり、
bは、0または1であり、
cは0、1または2であり、
dは、0または1である。) - 媒体は、正の誘電異方性を有し、式II~VIIIの化合物の群から選択される1種類以上の化合物を含むLCホスト混合物を含む、請求項1~4または9のいずれか1項に記載のLC媒体。
X20は、それぞれ同一または異なって、F、Cl、CN、SF5、SCN、NCS、それぞれ6個までのC原子を有するハロゲン化されたアルキル基、ハロゲン化されたアルケニル基、ハロゲン化されたアルコキシ基またはハロゲン化されたアルケニルオキシ基を表し、
Y20~24は、それぞれ同一または異なって、HまたはFを表し、
Z20は、-C2H4-、-(CH2)4-、-CH=CH-、-CF=CF-、-C2F4-、-CH2CF2-、-CF2CH2-、-CH2O-、-OCH2-、-COO-または-OCF2-、また式VおよびVIにおいては単結合も、また式VおよびVIIIにおいては-CF2O-も表し、
rは、0または1を表し、および
sは、0または1を表す。) - 媒体は、式DKおよびOの化合物の群から選択される1種類以上の化合物を含む、請求項1~4、9または10のいずれか1項に記載のLC媒体。
R5、R6、RO1およびRO2は、それぞれ同一または異なって、1~12個のC原子を有するアルキルを表し、該基において加えてO原子が互いに直接連結されないようにして、1個または2個の隣接しないCH2基は、-O-、-CH=CH-、-CO-、-OCO-または-COO-で置き換えられてよく、
ZO2は、CH2O、-C(O)O-、-CH2CH2-、-CF2CF2-または単結合を表し、
oは、1またh2であり、
eは、1または2である。) - 電気光学ディスプレイ、外部空間から内部空間へのエネルギーの通過を制御するためのデバイス、電子半導体、有機電界効果トランジスタ(OFETs:organic field-effect transistors)、プリント回路、無線周波数識別素子(RFIDs:radio frequency identification elements)、有機発光ダイオード(OLEDs:organic light-emitting diodes)、照明素子、光起電素子、光学センサー、効果顔料、装飾素子におけるまたはポリマーを着色するための色素としての請求項5~8のいずれか1項に記載の化合物の使用。
- 外部空間から内部空間へのエネルギーの通過を制御するためのデバイスであって、請求項1~4または9~13のいずれか1項に記載のLC媒体を含むスイッチ層を含むデバイス。
- 請求項15に記載のデバイスを含む窓。
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PCT/EP2019/075458 WO2020064591A1 (en) | 2018-09-25 | 2019-09-23 | Azo dye |
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Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016522442A (ja) | 2013-05-24 | 2016-07-28 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 二色性色素化合物を含むエネルギー通過調節用デバイス |
Family Cites Families (64)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3388114A (en) | 1964-07-20 | 1968-06-11 | Daito Chemical Industry Co Ltd | Azo dyes derived from 4-amino benzothiazole-or benzothiadiazole groups |
JPS55123673A (en) | 1979-03-16 | 1980-09-24 | Mitsui Toatsu Chem Inc | Liquid crystal color display device |
JPS55152875A (en) | 1979-05-14 | 1980-11-28 | Mitsubishi Chem Ind | Anthraquinone dyestuff for cellulose containing fibers |
JPS5652440U (ja) | 1979-09-29 | 1981-05-09 | ||
GB2065695B (en) | 1979-10-12 | 1984-07-25 | Hitachi Ltd | Guest-host type liquid crystal composition and liquid crystal display device using the same |
JPS5657850A (en) | 1979-10-18 | 1981-05-20 | Nippon Kanko Shikiso Kenkyusho:Kk | Azo compound and dichromatic dye for liquid crystal consisting of the same |
GB2065158A (en) | 1979-12-13 | 1981-06-24 | Standard Telephones Cables Ltd | Anthraquinone Dichroic Dyes |
JPS56104984A (en) | 1980-01-24 | 1981-08-21 | Nippon Kanko Shikiso Kenkyusho:Kk | Bichromic pigment for yellow liquid crystal |
DE3007198A1 (de) | 1980-02-26 | 1981-09-03 | Siemens AG, 1000 Berlin und 8000 München | Pleochroitischer anthrachinon-farbstoff, verfahren zu seiner herstellung und verwendung des farbstoffs |
US4350603A (en) | 1980-06-30 | 1982-09-21 | General Electric Company | Novel tris-azo dyes and liquid crystal compositions made therewith |
EP0043904A3 (de) | 1980-07-10 | 1982-03-31 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Farbstoffhaltige Mischungen, neue Farbstoffe und deren Verwendung in Flüssigkristallmischungen |
DE3069220D1 (en) | 1980-07-29 | 1984-10-25 | Ici Plc | Anthraquinone compounds and process for their preparation |
GB2082196B (en) | 1980-07-29 | 1985-01-23 | Secr Defence | Liquid crystal materials containing anthraquinone pleochroic dyes |
GB2081736B (en) | 1980-07-29 | 1985-02-20 | Secr Defence | Liquid crystal materials containing diamino-dihydroxy anthraquinone pleochroic dyes |
US4308161A (en) | 1980-08-04 | 1981-12-29 | General Electric Company | Novel yellow azo dyes and dichroic liquid crystal compositions made therewith |
EP0047027A1 (de) | 1980-08-22 | 1982-03-10 | BBC Aktiengesellschaft Brown, Boveri & Cie. | Flüssigkristallmischung |
JPS5755984A (en) | 1980-09-22 | 1982-04-03 | Hitachi Ltd | Liquid crystal composition |
JPS5763377A (en) | 1980-10-03 | 1982-04-16 | Mitsui Toatsu Chem Inc | Liquid crystal composition for color display |
DE3040102A1 (de) | 1980-10-24 | 1982-06-03 | Merck Patent Gmbh, 6100 Darmstadt | Dichroitische anthrachinonfarbstoffe, diese enthaltende fluessigkristalline dielektrika und elektrooptisches anzeigeelement |
US4308162A (en) | 1980-12-08 | 1981-12-29 | General Electric Company | Novel yellow azo dyes and dichroic liquid crystal compositions made therewith |
DE3046904A1 (de) | 1980-12-12 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Anthrachinonfarbstoffe, verfahren zu ihrer herstellung ihre verwendung sowie fluessigkristalline materialien enthaltend anthrachinonfarbstoffe |
EP0056492B1 (de) | 1981-01-10 | 1984-12-12 | BASF Aktiengesellschaft | Farbstoffe für Flüssigkristallmischungen |
DE3115147A1 (de) | 1981-04-15 | 1982-11-04 | Basf Ag, 6700 Ludwigshafen | Farbstoffe fuer fluessigkristallmischungen |
JPS57126879A (en) | 1981-01-12 | 1982-08-06 | Sumitomo Chem Co Ltd | Liquid crystal display element |
GB2094825B (en) | 1981-01-17 | 1984-09-12 | Mitsubishi Chem Ind | Liquid crystal compositions containing pleochroic anthraquinone dyes |
EP0059036B1 (en) | 1981-02-25 | 1987-07-29 | Imperial Chemical Industries Plc | Pleochroic anthraquinone dyes |
GB2094822B (en) | 1981-02-25 | 1986-03-05 | Ici Plc | Anthraquinone dyes |
DE3110960A1 (de) | 1981-03-20 | 1982-09-30 | Basf Ag, 6700 Ludwigshafen | Elektrophotographisches aufzeichnungsmaterial |
DE3115762A1 (de) | 1981-04-18 | 1982-11-11 | Merck Patent Gmbh, 6100 Darmstadt | "dichroitische anthrachinonfarbstoffe, diese enthaltende fluessigkristalline dielektrika und elektrooprisches anzeigeelement" |
DE3123519A1 (de) | 1981-06-13 | 1982-12-30 | Bayer Ag, 5090 Leverkusen | Fluessigkristallines material enthaltend azofarbstoffe |
JPS581775A (ja) | 1981-06-26 | 1983-01-07 | Mitsubishi Chem Ind Ltd | 液晶組成物 |
DE3126108A1 (de) | 1981-07-02 | 1983-01-20 | Merck Patent Gmbh, 6100 Darmstadt | "fluessigkristallines dielektrikum, neue dichroitische naphthochinonfarbstoffe und elektrooptisches anzeigeelement" |
DE3202761A1 (de) | 1982-01-28 | 1983-08-04 | Merck Patent Gmbh, 6100 Darmstadt | Fluessigkristallines dielektrikum, neue farbstoffe, verfahren zu ihrer herstellung und elektrooptisches anzeigeelement |
US6025897A (en) | 1993-12-21 | 2000-02-15 | 3M Innovative Properties Co. | Display with reflective polarizer and randomizing cavity |
JPH07181439A (ja) | 1993-12-24 | 1995-07-21 | Hitachi Ltd | アクティブマトリクス型液晶表示装置 |
JP3543351B2 (ja) | 1994-02-14 | 2004-07-14 | 株式会社日立製作所 | アクティブマトリクス型液晶表示装置 |
TW262553B (ja) | 1994-03-17 | 1995-11-11 | Hitachi Seisakusyo Kk | |
EP0698649A1 (de) | 1994-08-26 | 1996-02-28 | Basf Aktiengesellschaft | Verwendung von thermoplastisch verarbeitbaren, langzeitstabilen elektrolumineszenten Materialien |
WO1996023851A1 (de) | 1995-02-03 | 1996-08-08 | Merck Patent Gmbh | Elektrooptische flüssigkristallanzeige |
DE19528107B4 (de) | 1995-03-17 | 2010-01-21 | Merck Patent Gmbh | Flüssigkristallines Medium und seine Verwendung in einer elektrooptischen Flüssigkristallanzeige |
DE19528106A1 (de) | 1995-02-03 | 1996-08-08 | Merck Patent Gmbh | Elektrooptische Flüssigkristallanzeige |
DE19509410A1 (de) | 1995-03-15 | 1996-09-19 | Merck Patent Gmbh | Elektrooptische Flüssigkristallanzeige |
WO1997017415A1 (fr) | 1995-11-10 | 1997-05-15 | Mitsubishi Chemical Corporation | Composition de cristaux liquides et element d'affichage a cristaux liquides |
JPH09137166A (ja) | 1995-11-10 | 1997-05-27 | Chisso Corp | 液晶組成物及び液晶表示素子 |
US6099758A (en) | 1997-09-17 | 2000-08-08 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Broadband reflective polarizer |
US7023602B2 (en) | 1999-05-17 | 2006-04-04 | 3M Innovative Properties Company | Reflective LCD projection system using wide-angle Cartesian polarizing beam splitter and color separation and recombination prisms |
EP1378557B1 (de) | 2002-07-06 | 2007-02-21 | MERCK PATENT GmbH | Flüssigkristallines Medium |
DE112004000820T5 (de) * | 2003-05-16 | 2006-03-23 | Dow Global Technologies, Inc., Midland | Verfahren zur Herstellung eines 4,7-Bis(Halogenthien-2-YL)-2,1,3-Benzothiadiazols und eines Vorläufers davon |
EP1843407A1 (de) | 2006-04-07 | 2007-10-10 | Basf Aktiengesellschaft | Flüssig-kristalline Rylentetracarbonsäurederivate und deren Verwendung |
US7826009B2 (en) | 2006-12-21 | 2010-11-02 | 3M Innovative Properties Company | Hybrid polarizer |
WO2009141295A1 (en) | 2008-05-21 | 2009-11-26 | Technische Universiteit Eindhoven | Optical device with anisotropic luminescent material |
CN101324752B (zh) * | 2008-07-21 | 2012-07-25 | 上海天臣防伪技术股份有限公司 | 可以记录反射全息的聚合物液晶感光材料制备方法 |
EP2166040A1 (en) | 2008-09-22 | 2010-03-24 | Radiant Color N.V. | Novel lipophilic fluorescent dyes and a process for their production |
WO2010118422A2 (en) | 2009-04-10 | 2010-10-14 | Ravenbrick, Llc | Thermally switched optical filter incorporating a guest-host architecture |
WO2012079676A1 (de) | 2010-12-17 | 2012-06-21 | Merck Patent Gmbh | Flüssigkristallines medium |
WO2013004677A1 (en) | 2011-07-05 | 2013-01-10 | Peer+ B.V. | Liquid crystal dye mixture |
ITMI20111516A1 (it) * | 2011-08-08 | 2013-02-09 | Eni Spa | Procedimento per la preparazione di composti benzoetero[1,3]diazolici disostituiti con gruppi eteroarilici |
CN104837959B (zh) | 2012-12-13 | 2017-09-19 | 默克专利股份有限公司 | 液晶介质 |
JP6135608B2 (ja) | 2014-06-25 | 2017-05-31 | トヨタ自動車株式会社 | 車両用駆動装置 |
JP2018501361A (ja) * | 2014-12-19 | 2018-01-18 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 液晶媒体およびそれを含む高周波数素子 |
DE102015005800A1 (de) * | 2015-05-06 | 2016-11-10 | Merck Patent Gmbh | Thiadiazolochinoxalinderivate |
CN108884390B (zh) | 2016-04-08 | 2022-05-31 | 默克专利股份有限公司 | 用于合成功能性材料的中间体和工序 |
US10982150B2 (en) | 2016-06-28 | 2021-04-20 | Merck Patent Gmbh | Liquid crystalline medium |
US11168257B2 (en) | 2016-07-19 | 2021-11-09 | Merck Patent Gmbh | Liquid crystalline medium |
-
2019
- 2019-09-23 WO PCT/EP2019/075458 patent/WO2020064591A1/en unknown
- 2019-09-23 CN CN201980061899.9A patent/CN113195684A/zh active Pending
- 2019-09-23 JP JP2021516791A patent/JP7447099B2/ja active Active
- 2019-09-23 EP EP19779407.6A patent/EP3856869B1/en active Active
- 2019-09-23 KR KR1020217012133A patent/KR20210069062A/ko unknown
- 2019-09-23 US US17/278,953 patent/US11702597B2/en active Active
- 2019-09-24 TW TW108134400A patent/TWI835865B/zh active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016522442A (ja) | 2013-05-24 | 2016-07-28 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 二色性色素化合物を含むエネルギー通過調節用デバイス |
Non-Patent Citations (1)
Title |
---|
T.SUBASH SUNDAR,Rationally designed donnor-acceptor scheme based molecules for applications in opto-electronic devices,PHYSICAL CHEMISTRY CHEMICAL PHYSICS,18,13,9133-9147 |
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