TWI769141B - 對掌性化合物 - Google Patents
對掌性化合物 Download PDFInfo
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- TWI769141B TWI769141B TW105132206A TW105132206A TWI769141B TW I769141 B TWI769141 B TW I769141B TW 105132206 A TW105132206 A TW 105132206A TW 105132206 A TW105132206 A TW 105132206A TW I769141 B TWI769141 B TW I769141B
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- liquid crystal
- formula
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 174
- 239000000203 mixture Substances 0.000 claims abstract description 130
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 98
- -1 diagnostics Substances 0.000 claims abstract description 72
- 239000002019 doping agent Substances 0.000 claims abstract description 47
- 229920000642 polymer Polymers 0.000 claims abstract description 14
- 230000003287 optical effect Effects 0.000 claims abstract description 11
- 239000002537 cosmetic Substances 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 229920000106 Liquid crystal polymer Polymers 0.000 claims abstract description 5
- 238000003860 storage Methods 0.000 claims abstract description 5
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims abstract description 4
- 239000000853 adhesive Substances 0.000 claims abstract description 4
- 230000001070 adhesive effect Effects 0.000 claims abstract description 4
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 4
- 229920003002 synthetic resin Polymers 0.000 claims abstract description 4
- 239000000057 synthetic resin Substances 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- 229910052801 chlorine Inorganic materials 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 14
- 230000003098 cholesteric effect Effects 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 238000006359 acetalization reaction Methods 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 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 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 claims 1
- 239000000049 pigment Substances 0.000 abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000012071 phase Substances 0.000 description 35
- 239000000460 chlorine Substances 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
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- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- 239000002904 solvent Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000006850 spacer group Chemical group 0.000 description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 4
- VWSBGGRCEQOTNU-UHFFFAOYSA-N 7-bromonaphthalen-2-ol Chemical compound C1=CC(Br)=CC2=CC(O)=CC=C21 VWSBGGRCEQOTNU-UHFFFAOYSA-N 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004296 chiral HPLC Methods 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000004780 naphthols Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 description 3
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- 229910020898 NaBO2.4H2O Inorganic materials 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- NVKNRCHQLYVYFQ-UHFFFAOYSA-N OC1=C(C2=CC(=CC=C2C=C1)C1=CC=CC2=CC=CC=C12)C1=C(C=CC2=CC=C(C=C12)C1=CC=CC2=CC=CC=C12)O Chemical group OC1=C(C2=CC(=CC=C2C=C1)C1=CC=CC2=CC=CC=C12)C1=C(C=CC2=CC=C(C=C12)C1=CC=CC2=CC=CC=C12)O NVKNRCHQLYVYFQ-UHFFFAOYSA-N 0.000 description 3
- 229910002666 PdCl2 Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000004904 UV filter Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000005529 alkyleneoxy group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Chemical group 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 3
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- CPTIBDHUFVHUJK-NZYDNVMFSA-N mitopodozide Chemical compound C1([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H](CO)[C@@H]2C(=O)NNCC)=CC(OC)=C(OC)C(OC)=C1 CPTIBDHUFVHUJK-NZYDNVMFSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000005691 oxidative coupling reaction Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
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- 238000010561 standard procedure Methods 0.000 description 3
- 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 3
- 230000009466 transformation Effects 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- SJSRFXJWBKOROD-UHFFFAOYSA-N 1,1'-bi(cyclohexyl)-1-carboxylic acid Chemical compound C1CCCCC1C1(C(=O)O)CCCCC1 SJSRFXJWBKOROD-UHFFFAOYSA-N 0.000 description 2
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 description 2
- ITBIOYSBOSGNCZ-UHFFFAOYSA-N 2-methoxy-7-naphthalen-2-ylnaphthalene Chemical group C1=CC=CC2=CC(C=3C=CC4=CC=C(C=C4C=3)OC)=CC=C21 ITBIOYSBOSGNCZ-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- UNFNRIIETORURP-UHFFFAOYSA-N 7-methoxynaphthalen-2-ol Chemical compound C1=CC(O)=CC2=CC(OC)=CC=C21 UNFNRIIETORURP-UHFFFAOYSA-N 0.000 description 2
- 229910015845 BBr3 Inorganic materials 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- QKHWNVRKLGWLSP-UHFFFAOYSA-N C(CC)C1CCC(CC1)C1=CC=C(C=C1)C1=CC=C2C=CC(=CC2=C1)O Chemical compound C(CC)C1CCC(CC1)C1=CC=C(C=C1)C1=CC=C2C=CC(=CC2=C1)O QKHWNVRKLGWLSP-UHFFFAOYSA-N 0.000 description 2
- WXWIGJIHIWZNTE-UHFFFAOYSA-N C1OC2=C(C3=CC(=CC=C3C=C2)C2=CC=C(C=C2)C2CCC(CC2)CCC)C2=C(C=CC3=CC=C(C=C23)C2=CC=C(C=C2)C2CCC(CC2)CCC)O1 Chemical compound C1OC2=C(C3=CC(=CC=C3C=C2)C2=CC=C(C=C2)C2CCC(CC2)CCC)C2=C(C=CC3=CC=C(C=C23)C2=CC=C(C=C2)C2CCC(CC2)CCC)O1 WXWIGJIHIWZNTE-UHFFFAOYSA-N 0.000 description 2
- RJDHCVLRMUWADL-UHFFFAOYSA-N C1OC2=C(C3=CC(=CC=C3C=C2)C2=CC=C(C=C2)C2CCC(CC2)CCC)C2=C(C=CC3=CC=CC=C23)O1 Chemical group C1OC2=C(C3=CC(=CC=C3C=C2)C2=CC=C(C=C2)C2CCC(CC2)CCC)C2=C(C=CC3=CC=CC=C23)O1 RJDHCVLRMUWADL-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-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
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- QTBUVZSHCNAPRT-UHFFFAOYSA-N [4-(4-propylcyclohexyl)phenyl]boronic acid Chemical compound C1CC(CCC)CCC1C1=CC=C(B(O)O)C=C1 QTBUVZSHCNAPRT-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 239000012952 cationic photoinitiator Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 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 2
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- 150000002500 ions Chemical class 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 239000002243 precursor Substances 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- IWIOHRVOBOYWQE-UHFFFAOYSA-N (1-cyclohexylcyclohexyl)benzene Chemical compound C1CCCCC1C1(C=2C=CC=CC=2)CCCCC1 IWIOHRVOBOYWQE-UHFFFAOYSA-N 0.000 description 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- PWGUTKLGUISGAE-UHFFFAOYSA-N (4-propylcyclohexyl)benzene Chemical compound C1CC(CCC)CCC1C1=CC=CC=C1 PWGUTKLGUISGAE-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
- C09K19/588—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems
-
- 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
-
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/323—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a binaphthyl
-
- 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
- C09K2019/343—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a seven-membered ring
- C09K2019/3433—Seven-membered ring with oxygen(s) in fused, bridged or spiro ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polarising Elements (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15188556 | 2015-10-06 | ||
| EP15188556.3 | 2015-10-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201734186A TW201734186A (zh) | 2017-10-01 |
| TWI769141B true TWI769141B (zh) | 2022-07-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW105132206A TWI769141B (zh) | 2015-10-06 | 2016-10-05 | 對掌性化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10982149B2 (https=) |
| EP (1) | EP3359625B1 (https=) |
| JP (1) | JP6913084B2 (https=) |
| KR (1) | KR102665013B1 (https=) |
| CN (1) | CN108138052B (https=) |
| TW (1) | TWI769141B (https=) |
| WO (1) | WO2017059942A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI662112B (zh) * | 2017-04-21 | 2019-06-11 | 友達光電股份有限公司 | 藍相液晶顯示器、其製造方法、以及其所使用的對掌性材料 |
| CN109912560B (zh) * | 2018-12-14 | 2021-03-23 | 陕西师范大学 | 一类具有聚集诱导发光效应和圆偏振的荧光材料及其制备方法 |
| KR102249676B1 (ko) * | 2019-10-10 | 2021-05-07 | 전북대학교산학협력단 | 유연성 및 가공성이 우수한 블랙아이스 표시용 대면적 광학필름 및 롤투롤 연속공정을 이용한 이의 제조방법 |
| KR20220124474A (ko) * | 2021-03-03 | 2022-09-14 | 한양대학교 산학협력단 | 선택적 광 반사 디스플레이 및 그의 제조방법 |
| WO2026018477A1 (ja) * | 2024-07-17 | 2026-01-22 | 株式会社村田製作所 | ビナフチル誘導体、液晶組成物、液晶素子、表示装置および調光装置 |
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|---|---|---|---|---|
| CN1509280A (zh) * | 2001-05-21 | 2004-06-30 | Ĭ��ר���ɷ�����˾ | 手性化合物 |
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| EP0261712A1 (en) | 1986-09-04 | 1988-03-30 | Koninklijke Philips Electronics N.V. | Picture display cell, method of forming an orientation layer on a substrate of the picture display cell and monomeric compounds for use in the orientation layer |
| US5453863A (en) | 1991-05-02 | 1995-09-26 | Kent State University | Multistable chiral nematic displays |
| ATE178645T1 (de) | 1991-05-02 | 1999-04-15 | Univ Kent State Ohio | Flüssigkristall lichtmodulierungs-vorrichtung und -material |
| EP0591508B2 (en) | 1992-04-27 | 2003-01-15 | MERCK PATENT GmbH | Electrooptical liquid crystal system |
| ES2129463T3 (es) | 1992-05-18 | 1999-06-16 | Univ Kent State Ohio | Dispositivo y material cristalinos y liquidos de modulacion de luz. |
| TW289095B (https=) | 1993-01-11 | 1996-10-21 | ||
| GB2279659B (en) | 1993-07-05 | 1998-04-22 | Merck Patent Gmbh | Liquid crystalline material |
| DE4342280A1 (de) | 1993-12-11 | 1995-06-14 | Basf Ag | Polymerisierbare chirale Verbindungen und deren Verwendung |
| DE4405316A1 (de) | 1994-02-19 | 1995-08-24 | Basf Ag | Neue polymerisierbare flüssigkristalline Verbindungen |
| DE19504224A1 (de) | 1994-02-23 | 1995-08-24 | Merck Patent Gmbh | Flüssigkristallines Material |
| US5493430A (en) | 1994-08-03 | 1996-02-20 | Kent Display Systems, L.P. | Color, reflective liquid crystal displays |
| DE19532408A1 (de) | 1995-09-01 | 1997-03-06 | Basf Ag | Polymerisierbare flüssigkristalline Verbindungen |
| GB2329636B (en) | 1996-07-01 | 2000-07-19 | Merck Patent Gmbh | Chiral dopants |
| FR2750599B1 (fr) | 1996-07-02 | 1998-12-31 | Oreal | Nouvelles compositions cosmetiques comprenant des agents de coloration cristaux liquides et leur utilisation |
| DE19629761A1 (de) | 1996-07-23 | 1997-06-05 | Wacker Chemie Gmbh | Zubereitungen mit vom Betrachtungswinkel abhängiger Farbigkeit |
| DE19834162A1 (de) | 1997-08-13 | 1999-02-18 | Merck Patent Gmbh | Chirale Verbindungen |
| DE19913604A1 (de) | 1999-03-25 | 2000-09-28 | Basf Ag | Chirale Verbindungen und deren Verwendung als chirale Dotierstoffe zur Herstellung von cholesterisch-flüssigkristallinen Zusammensetzungen |
| EP1326854B1 (en) | 2000-10-20 | 2004-06-23 | MERCK PATENT GmbH | Chiral binaphthol derivatives |
| JP2002179669A (ja) * | 2000-12-14 | 2002-06-26 | Fuji Photo Film Co Ltd | 光学活性化合物、光反応型キラル剤、液晶組成物、液晶の捻れ構造を変化させる方法、液晶の螺旋構造を固定化する方法、液晶カラーフィルタ、光学フィルム及び記録媒体 |
| EP1260528A1 (en) | 2001-05-21 | 2002-11-27 | Borealis Technology OY | Propylene polymer pipes for pipelines |
| JP5841301B2 (ja) | 2002-11-15 | 2016-01-13 | 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 | 電気光学的光変調素子、電気光学的ディスプレイおよび変調媒体 |
| DE10253606A1 (de) * | 2002-11-15 | 2004-05-27 | Merck Patent Gmbh | Elektrooptisches Lichtsteuerelement, elektrooptische Anzeige und Steuermedium |
| US7597942B2 (en) * | 2004-09-06 | 2009-10-06 | Merck Patent Gmbh | Polymerisable liquid crystal material |
| CN101277943B (zh) * | 2005-09-30 | 2012-05-23 | 默克专利股份有限公司 | 手性化合物 |
| JP6058644B2 (ja) | 2011-06-01 | 2017-01-11 | 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 | 液晶媒体および液晶ディスプレイ |
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| JP6386378B2 (ja) | 2011-09-06 | 2018-09-05 | 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 | 液晶媒体および液晶ディスプレイ |
| KR20150002847A (ko) | 2012-04-20 | 2015-01-07 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
| EP2708587B1 (en) | 2012-09-18 | 2015-07-15 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| EP2904068B1 (en) | 2012-10-02 | 2016-10-12 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| CN103030625B (zh) * | 2012-11-12 | 2015-09-16 | 石家庄诚志永华显示材料有限公司 | 联萘二酚手性化合物及其制备方法与应用 |
| EP2986688B1 (en) | 2013-04-19 | 2017-04-19 | Merck Patent GmbH | Mesogenic compound, liquid crystal medium and liquid crystal display |
| JP6576350B2 (ja) | 2013-12-30 | 2019-09-18 | 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 | 液晶媒体および液晶ディスプレイ |
-
2016
- 2016-09-07 CN CN201680058075.2A patent/CN108138052B/zh active Active
- 2016-09-07 WO PCT/EP2016/001510 patent/WO2017059942A1/en not_active Ceased
- 2016-09-07 JP JP2018517737A patent/JP6913084B2/ja active Active
- 2016-09-07 US US15/766,175 patent/US10982149B2/en active Active
- 2016-09-07 EP EP16762728.0A patent/EP3359625B1/en active Active
- 2016-09-07 KR KR1020187013040A patent/KR102665013B1/ko active Active
- 2016-10-05 TW TW105132206A patent/TWI769141B/zh active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1509280A (zh) * | 2001-05-21 | 2004-06-30 | Ĭ��ר���ɷ�����˾ | 手性化合物 |
Also Published As
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| US20180291271A1 (en) | 2018-10-11 |
| JP2018538236A (ja) | 2018-12-27 |
| WO2017059942A1 (en) | 2017-04-13 |
| EP3359625A1 (en) | 2018-08-15 |
| CN108138052B (zh) | 2022-04-12 |
| CN108138052A (zh) | 2018-06-08 |
| EP3359625B1 (en) | 2019-10-23 |
| JP6913084B2 (ja) | 2021-08-04 |
| TW201734186A (zh) | 2017-10-01 |
| KR102665013B1 (ko) | 2024-05-13 |
| KR20180067591A (ko) | 2018-06-20 |
| US10982149B2 (en) | 2021-04-20 |
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